Synthesis of Penems

  • Ettore Perrone
  • Giovanni Franceschi

Abstract

The synthesis of penems has been the object of intensive research in the last decade. Stereoselective synthesis of azetidinones, chemoselective cleavage of the thiazolidine ring of penicillins, hydroxy- ethylation at the lactam α-carbon, and penem annulation reactions are the important issues addressed in this work. By confronting possibilities with achievements, a comprehensive but readable survey of this chapter of antibiotic chemistry is attempted.

Keywords

Disulfide Lactone Bromo Acetoacetate Silyl 

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References

  1. 1.
    Woodward RB (1977) In: Elks J (ed) Recents Advances in the Chemistry of β-Lactam Antibiotics The Royal Society of Chemistry, Special Publication No 28, London, p 167Google Scholar
  2. 2.
    Wise R (1987) Lancet 1251Google Scholar
  3. 3.
    Sheehan JC, Henery-Logan KR (1962) J Am Chem Soc 84: 2983Google Scholar
  4. 4.
    Bose AK, Spiegelmann G, Manhas MS (1968) J Am Chem Soc 90: 4506Google Scholar
  5. 5.
    Pfaendler HR, Gosteli J, Woodward RB, Rihs G (1981) J Am Chem Soc 103: 4526Google Scholar
  6. 6.
    Cassinelli G, Corigli R, Orezzi P, Ventrella G, Bedeschi A, Perrone E, Borghi D, Franceschi G (1988) J Antibiotics 41: 984Google Scholar
  7. 7.
    Sugita O, Yonemoto Y, Morozumi N, Iwata H, Ohnuma N, Noguchi T (1989) 29th Intersci Conf Antimicrob Agents Chemother (Houston), Program and Abstracts, the American Society of Microbiology, p 114Google Scholar
  8. 8.
    Visentin G, Perrone E (1989) Unpublished resultsGoogle Scholar
  9. 9.
    Malatesta V (private communication)Google Scholar
  10. 10.
    Clauss K, Grimm D, Prossel G (1974) Liebigs Ann Chem 539Google Scholar
  11. 11. (a)
    Seebach D, Züger M (1982) Helv Chim Acta 65:495Google Scholar
  12. 11. (b)
    Noyori R, Ohkuma T, Kitamura M, Takaya H, Sayo N, Kumobayashi H, Akutagawa S (1987) J Am Chem Soc 109: 5856Google Scholar
  13. 12. (a)
    Ohashi T, Kan K, Sada I, Miyama A, Watanabe K (1986) Eur Pat Appl 167,154 and 167,155Google Scholar
  14. 12. (b)
    Sada I, Kan K, Ueyama N, Matsunobu S, Ohashi T, Watanabe K (1988) Eur Pat Appl 280,962Google Scholar
  15. 13.
    Ishiguro M, Iwata K, Nakatsuka T, Tanaka R, Maeda Y, Nishibara T, Noguchi T (1988) J Antibiotics 51: 1685Google Scholar
  16. 14.
    Hungerbüler E, Kalvoda J, Scartazzini R, Schneider P, Lang M (1988) EUCHEM Symposium on the Chemical Synthesis of Antibiotics (Aussois, France)Google Scholar
  17. 15.
    Staudinger H (1907) Liebigs Ann Chem 356: 51Google Scholar
  18. 16. (a)
    Bose AK, Spiegelman G, Manhas MS (1968) J Am Chem Soc 90: 4506Google Scholar
  19. 16. (b)
    Wagle DR, Garai C, Chiang J, Monteleone MG, Kurys BE, Strohmeyer TW, Hegde VR, Manhas MS, Bose AK (1988) J Org Chem 53: 4277, and ref. thereinGoogle Scholar
  20. 17.
    Ito Y, Kawabata T, Terashima S (1986) Tetrahedron Lett 27: 5751Google Scholar
  21. 18. (a)
    Tschaen DM, Fuentes LM, Lynch JE, Laswell WL, Volante RP, Shinkai I (1988) Tetrahedron Lett 29: 2799Google Scholar
  22. 18. (b)
    Desmond R, Mills S, Volante RP, Shinkai I (1989) Synth Commun 19: 379Google Scholar
  23. 19.
    Gilman H, Speeter M (1943) J Am Chem Soc 65: 2255Google Scholar
  24. 20. (a)
    Hart DJ, Kanai K, Thomas DT, Yang T-K (1983) J Org Chem 48: 289Google Scholar
  25. 20. (b)
    Ha D-C, Hart DJ, Yang T-K (1984) J Am Chem Soc 106: 4819Google Scholar
  26. 20. (c)
    Hart DJ, Ha D-C (1985) Tetrahedron Lett 26: 5493Google Scholar
  27. 21. (a)
    Georg GI (1984) Tetrahedron Lett 25: 3779Google Scholar
  28. 21. (b)
    Georg GI, Gill HS, Gerhardt C (1985) Tetrahedron Lett 26: 3903Google Scholar
  29. 21. (c)
    Georg GI, Kant J, Gill HS (1987) J Am Chem Soc 109: 1129Google Scholar
  30. 22. (a)
    Chiba T, Nagatsuma M, Nakai T (1984) Chem Lett 1927Google Scholar
  31. 22. (b)
    Chiba T, Nakai T (1985) Chem Lett 651Google Scholar
  32. 22. (c)
    Chiba T, Nagatsuma M, Nakai T (1985) Chem Lett 1343Google Scholar
  33. 22. (d)
    Chiba T, Nakai T (1985) Tetrahedron Lett 26: 4647Google Scholar
  34. 23. (a)
    Cainelli G, Contento M, Giacomini D, Panunzio M (1985) Tetrahedron Lett 26: 937Google Scholar
  35. 23. (b)
    Cainelli G, Giacomini D, Panunzio M, Martelli G, Spunta G (1987) Tetrahedron Lett 28: 3593Google Scholar
  36. 23. (c)
    Battaglia A, Cainelli G, Giacomini D, Martelli G, Panunzio M (1987) Tetrahedron Lett 28: 4347Google Scholar
  37. 23. (d)
    Cainelli G, Giacomini D, Panunzio M, Martelli G, Spunta G (1987) Tetrahedron Lett 28: 5369Google Scholar
  38. 23. (e)
    Cainelli G, Panunzio M (1988) J Am Chem Soc 110: 6879Google Scholar
  39. 24. (a)
    Iimori T, Shibasaki M (1985) Tetrahedron Lett 26: 1523Google Scholar
  40. 24. (b)
    Iimori T, Ishida Y, Shibasaki M (1986) Tetrahedron Lett 27: 2149Google Scholar
  41. 24. (c)
    Iimori T, Shibasaki M (1986) Tetrahedron Lett 27: 2153Google Scholar
  42. 24. (d)
    Mori M, Kagechika K, Tohjima K, Shibasaki M (1988) Tetrahedron Lett 29: 1409Google Scholar
  43. 25. (a)
    Hirai K, Naito A (1989) Tetrahedron Lett 30:1107Google Scholar
  44. 25. (b)
    Hirai K, Miyakoshi S, Naito A (1989) Tetrahedron Lett 30: 2555Google Scholar
  45. 26.
    Kobayashi S, Iimori T, Izawa T, Ohno M (1981) J Am Chem Soc 103: 2406Google Scholar
  46. 27.
    Sheehan JC, Bose AK (1950) J Am Chem Soc 72: 5158Google Scholar
  47. 28. (a)
    Shiozaki M, Ishida N, Hiraoka T, Yanagisawa H (1981) Tetrahedron Lett 22: 5205Google Scholar
  48. 28. (b)
    Shiozaki M, Ishida N, Murayama H, Hiraoka T (1983) Tetrahedron 39: 2399Google Scholar
  49. 28. (c)
    Yanagisawa H, Ando A, Shiozaki M, Hiraoka T (1983) Tetrahedron Lett 24: 1037Google Scholar
  50. 28. (d)
    Yanagisawa H, Shiozaki M, Hiraoka T (1985) Bull Chem Soc Jpn 58: 3264Google Scholar
  51. 28. (e)
    Shiozaki M, Hiraoka T, Yanagisawa H (1986) Heterocycles 24: 1007Google Scholar
  52. 29. (a)
    Hanessian S, Bedeschi A, Battistini C, Mongelli N (1985) J Am Chem Soc 107: 1438Google Scholar
  53. 29. (b)
    Hanessian S, Bedeschi A, Battistini C, Mongelli N (1985) Lect Heterocycl Chem 8: 43Google Scholar
  54. 30.
    Chackalamannil S, Fett N, Kirkup M, Afonso A, Ganguly AK (1988) J Org Chem 53: 450Google Scholar
  55. 31.
    Gravestock MB (1988) Eur Pat Appl 265,169Google Scholar
  56. 32.
    Sheehan JC, Hess GP (1955) J Am Chem Soc 77: 1067Google Scholar
  57. 33.
    Salzmann TN, Ratcliffe R, Christensen BC, Bouffard FA (1980) J Am Chem Soc 102: 6161Google Scholar
  58. 34.
    Reider PJ, Grabowski EJJ (1982) Tetrahedron Lett 23: 2293Google Scholar
  59. 35.
    Allmendinger T, Rish G, Wetter H (1988) Helv Chim Acta 71: 395Google Scholar
  60. 36.
    Melillo DG, Shinkai I, Liu T, Ryan K, Sletzinger M (1980) Tetrahedron Lett 21: 2783Google Scholar
  61. 37. (a)
    Bersier J, Sedelmeier G (1988) EUCHEM Symposium on the Chemical Synthesis of Antibiotics (Aussois, France)Google Scholar
  62. 37. (b)
    Sedelmeier G, Bersier J (1988) Eur Pat Appl 279,781Google Scholar
  63. 38. (a)
    Kametani T, Huang S-P, Nakayama A, Honda K (1982) J Org Chem 47: 2328Google Scholar
  64. 38. (b)
    Ihara M, Takahashi M, Fukumoto K, Kametani T (1988) Heterocycles 27: 327, and references thereinGoogle Scholar
  65. 39.
    Kametani T, Chu S-D, Honda T (1988) J Chem Soc Perkin Trans 1 1593Google Scholar
  66. 40.
    Schneider P, Ramos G, Bersier J (1988) Eur Pat Appl 290,385Google Scholar
  67. 41. (a)
    Miller MJ (1986) Accts Chem Res 19: 49Google Scholar
  68. 41. (b)
    Miller MJ, Hsiao CN, Huang NZ, Kalish VJ, Peterson K, Rajendra G (1989) In: Bentley PH, Southgate R (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 70, London, p 273Google Scholar
  69. 42.
    Nagao Y, Kumagai T, Takao S, Hagiwara Y, Abe T, Ochiai M, Fujita E, Taga T, Aoyagi S, Nagase Y, Inoue Y (1985) 17th Congress of Heterocyclic Chemistry (Sapporo), Abstracts of Papers, p 247Google Scholar
  70. 43. (a)
    Kaneko T (1985) J Am Chem Soc 107: 5490Google Scholar
  71. 43. (b)
    Kaneko T, Okamoto Y, Hatada K (1987) J Chem Soc Chem Commun 1511Google Scholar
  72. 44.
    Casabuona F, Longo A, Crugnola A, Lombardi P (1981) Tetrahedron Lett 22: 4145Google Scholar
  73. 45.
    Pfaendler HR, Gosteli J, Woodward RB (1980) J Am Chem Soc 102: 2039Google Scholar
  74. 46. (a)
    Pfaendler HR (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 368Google Scholar
  75. 46. (b)
    Lang M, Hungerbüler E, Schneider P, Scartazzini R, Tosch W, Konopka EA, Zak O (1986) Helv Chim Acta 69: 1576Google Scholar
  76. 47.
    Sammes PG (1976) Chem Rev 76: 113Google Scholar
  77. 48.
    Ernest I, Gosteli J, Greengrass CW, Holick W, Jackman DE, Pfaendler HR, Woodward RB (1978) J Am Chem Soc 100: 8214Google Scholar
  78. 49.
    Ernest I, Gosteli J, Woodward RB (1979) J Am Chem Soc 101: 6301Google Scholar
  79. 50.
    Kukolja S (1971) J Am Chem Soc 93: 6267Google Scholar
  80. 51. (a)
    Banville J, Belleau B, Dextraze P, Douglas JL, Leitner F, Martel A, Menard M, Saintonge R, Ueda Y (1981) 182nd ACS National Meeting (New York, USA)Google Scholar
  81. 51. (b)
    Martel A, Collerette J, Banville J, Daris J-P, Lapointe P, Belleau B, Menard M (1983) Can J Chem 61: 613Google Scholar
  82. 51. (c)
    Menard M, Martel A (1980) UK Pat 2,041,524Google Scholar
  83. 52.
    Imuta M, Uyeo S, Nakano M, Yoshida T (1985) Chem Pharm Bull 33: 4371Google Scholar
  84. 53.
    Broom NJP, Coulton S, Francois I, Harbridge JB, Nayler JHL, Osborne NF (1989) In: Bentley PH, Southgate R (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 70, London, p 247Google Scholar
  85. 54. (a)
    Girijavallabhan VM, Ganguly AK, McCombie SW, Pinto P, Rizvi R (1981) Tetrahedron Lett 22: 3485Google Scholar
  86. 54. (b)
    Ganguly AK, Girijavallabhan VM, McCombie S, Pinto P, Rizvi R, Jeffrey PD, Lin S (1982) J Antimicrob Chemother 9 (Suppl C): 1Google Scholar
  87. 55.
    Alpegiani M, Bedeschi A, Foglio M, Giudici F, Perrone E (1983) Tetrahedron Lett: 24: 1627Google Scholar
  88. 56.
    Franceschi G, Foglio M, Alpegiani M, Battistini C, Bedeschi A, Perrone E, Zarini F, Arcamone C, Della Bruna C, Sanfilippo A (1983) J Antibiotics 36: 938Google Scholar
  89. 57.
    Endo M (1987) Can J Chem 65: 2140Google Scholar
  90. 58. (a)
    Stoodley RJ, Whitehouse NR (1973) J Chem Soc Perkin Trans 1 32Google Scholar
  91. 58. (b)
    Stoodley RJ, Whitehouse NR (1974) J Chem Soc Perkin Trans 1181Google Scholar
  92. 59.
    Kang J, Choi YR, Choi S-G, Cho HG, Lim D, Im WB, Lee JH (1988) Bull Korean Chem Soc 9: 403Google Scholar
  93. 60. (a)
    Oida S (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 330Google Scholar
  94. 60. (b)
    Yoshida A, Hayashi T, Takeda N, Oida S, Ohki E (1981) Chem Pharm Bull 29: 2899Google Scholar
  95. 61. (a)
    Hirai K, Iwano Y, Fujimoto K (1982) Heterocycles 17: 201Google Scholar
  96. 61. (b)
    Fujimoto K, Iwano Y, Hirai K, Sugawara S (1986) Chem Pharm Bull 34: 999Google Scholar
  97. 62.
    Leanza WJ, DiNinno F, Muthard DA, Wilkening RR, Wildonger KJ, Ratcliffe RW, Christensen BG (1983) Tetrahedron 39: 2505Google Scholar
  98. 63.
    Ganguly AK, Afonso A, Girijavallabhan VM, McCombie S (1985) J Antimicrob Chemother 15 (Suppl C): 1Google Scholar
  99. 64.
    Morin RB, Jackson BG, Mueller RA, Lavagino ER, Scanlon WB, Andrews SL (1969) J Am Chem Soc 91: 1401Google Scholar
  100. 65.
    Cooper RDG, Koppel GA (1982) In: Morin RB, Gorman M (eds) Chemistry and Biology of β-Lactam Antibiotics, Academic, New York, vol 1, p 1Google Scholar
  101. 66.
    Kapili LV, Kellogg MS, Martingano RJ (1981) Heterocycles 22: 3089Google Scholar
  102. 67.
    Suarato A, Lombardi P, Galliani C, Franceschi G (1978) Tetrahedron Lett 4059Google Scholar
  103. 68.
    Gosteli J, Holick W, Lang M, Woodward RB (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 359Google Scholar
  104. 69.
    Foglio M, Franceschi G (1981) Unpublished resultsGoogle Scholar
  105. 70.
    Alpegiani M, Bedeschi A, Foglio M, Perrone E (1983) Tetrahedron Lett 24: 1623Google Scholar
  106. 71.
    DiNinno F, Beattie TR, Christensen BG (1977) J Org Chem 42: 2960Google Scholar
  107. 72.
    Aimetti JA, Kellogg MS (1979) Tetrahedron Lett 3805Google Scholar
  108. 73.
    Kim WJ, Lee GS, Shim SC (1984) J Antibiotics 37: 1276Google Scholar
  109. 74. (a)
    Martel A, Daris JP, Bachand C, Menard M (1987) Can J Chem 65: 2179Google Scholar
  110. 74. (b)
    Martel A, Daris JP (1986) US Pat 4,596,677Google Scholar
  111. 75. (a)
    Wolfe S, Godfrey JC, Holdrege CT, Perron YG (1963) J Am Chem Soc 85: 643Google Scholar
  112. 75. (b)
    Wolfe S, Godfrey JC, Holdrege CT, Perron YG (1968) Can J Chem 46: 2549Google Scholar
  113. 76.
    Endo M (1987) Synth Commun 17: 1029Google Scholar
  114. 77. (a)
    Clayton JP, Nayler JHC, Southgate R, Tollyday P (1971) J Chem Soc Chem Commun 590Google Scholar
  115. 77. (b)
    Clayton JP, Nayler JHC, Pearson MJ, Southgate R (1974) J Chem Soc Perkin Trans 1 22Google Scholar
  116. 77. (c)
    Brain EHG, McMillan I, Nayler JHC, Southgate R, Tollyday P (1974) J Chem Soc Perkin Trans 1 562Google Scholar
  117. 78.
    Karady S, Amato JS, Reamer RA, Weinstock LM (1981) J Am Chem Soc 103: 6765Google Scholar
  118. 79.
    Mak C-P, Fliri H (1985) Tetrahedron Lett 26: 1433Google Scholar
  119. 80.
    Denerley PM, Thomas EJ (1979) J Chem Soc Perkin Trans 1 3175Google Scholar
  120. 81. (a)
    Alpegiani M, Bedeschi A, Giudici F, Perrone E, Franceschi G (1985) J Am Chem Soc 107: 6398Google Scholar
  121. 81. (b)
    Alpegiani M, Bedeschi A, Bissolino P, Visentin G, Perrone E, Franceschi G (1988) 4th Internat Symp Recent Advances in the Chemistry of β-Lactam Antibiotics (Cambridge, UK)Google Scholar
  122. 81. (c)
    Alpegiani M, Bedeschi A, Bissolino P, Visentin G, Zarini F, Perrone E, Franceschi G (1990) Heterocycles 31: (in press)Google Scholar
  123. 82. (a)
    Battistini C, Scarafile C, Foglio M, Franceschi G (1984) Tetrahedron Lett 25: 2395Google Scholar
  124. 82. (b)
    Perrone E, Alpegiani M, Bedeschi A, Giudici F, Franceschi G (1984) Tetrahedron Lett 25: 2399Google Scholar
  125. 83. (a)
    Yoshimoto M, Ishihara S, Nakayama E, Shoji E, Kuwano H, Soma N (1972) Tetrahedron Lett 4387Google Scholar
  126. 83. (b)
    Numata M, Imashiro Y, Minamida I, Yamaoka M (1972) Tetrahedron Lett 5079Google Scholar
  127. 84. (a)
    Kametani T, Kanaya N, Mochizuki T, Honda T (1983) Tetrahedron Lett 24: 1511Google Scholar
  128. 84. (b)
    Kametani T, Kanaya N, Nakayama A, Mochizuki T, Yokohama S, Honda T (1986) J Org Chem 51: 624Google Scholar
  129. 85. (a)
    Foglio M, Franceschi G, Scarafile C, Arcamone F (1980) J Chem Soc Chem Commun 70Google Scholar
  130. 85. (b)
    Franceschi G, Foglio M, Arcamone F, Sanfilippo A, Schioppacassi G (1980) J Antibiotics 33: 453Google Scholar
  131. 86.
    Hatfield LD, Fisher J, José FL, Cooper RDG (1970) Tetrahedron Lett 4897Google Scholar
  132. 87.
    Perrone E, Stoodley RJ (1982) J Chem Soc Chem Commun 933Google Scholar
  133. 88.
    Banville J, Lapointe P, Belleau B, Menard M (1988) Can J Chem 66: 1390Google Scholar
  134. 89.
    Kamiya T, Teraji T, Sato Y, Hashimoto M, Nakaguchi O, Oku T (1973) Tetrahedron Lett 3001Google Scholar
  135. 90.
    Ernest I (1980) Helv Chim Acta 63: 201Google Scholar
  136. 91.
    Prasad K, Hamberger H, Stütz P, Schulz G (1981) Helv Chim Acta 64: 279Google Scholar
  137. 92.
    Battistini C, Scarafile C, Vioglio S, Perrone E, Franceschi G (1986) Tetrahedron Lett 27: 513Google Scholar
  138. 93. (a)
    Irving JR, Perrone E, Stoodley RJ (1983) Tetrahedron Lett 24: 1429Google Scholar
  139. 93. (b)
    Irving JR, Perrone E, Stoodley RJ (1983) Tetrahedron Lett 24: 2501Google Scholar
  140. 94.
    Barton DHR, Coates IH, Sammes PG, Cooper CM (1973) J Chem Soc Chem Commun 303Google Scholar
  141. 95. (a)
    Foglio M, Franceschi G, Scarafile C, Zini P (1981) Heterocycles 16: 1919Google Scholar
  142. 95. (b)
    Foglio M, Battistini C, Zarini F, Franceschi G (1982) Heterocycles 19: 485Google Scholar
  143. 95. (c)
    Foglio M, Battistini C, Zarini F, Scarafile C, Franceschi G (1983) Heterocycles 20: 1491Google Scholar
  144. 96.
    Battistini C, Alpegiani M, Bedeschi A, Perrone E, Scarafile C, Franceschi G (1985) In: Brown AG, Roberts SM (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 52, London, p 357Google Scholar
  145. 97.
    Foglio M, Franceschi G, Serra-Errante G, Ballabio M, Arcamone F (1981) Heterocycles 15: 785Google Scholar
  146. 98. (a)
    Pant CM, Steele J, Stoodley RJ (1982) J Chem Soc Perkin Trans 1, 595Google Scholar
  147. 98. (b)
    Steele J, Stoodley RJ (1983) J Chem Soc Perkin Trans 1, 2241Google Scholar
  148. 99.
    Welch WM, Guarino JC (1987) J Org Chem 52: 4401Google Scholar
  149. 100.
    Maruyama H, Hiraoka T (1986) J Org Chem 51: 399Google Scholar
  150. 101. (a)
    Hirai K, Iwano Y, Fujimoto K (1982) Tetrahedron Lett 23: 4021Google Scholar
  151. 101. (b)
    Fujimoto K, Iwano Y, Hirai K (1986) Bull Chem Soc Jpn 59: 1887Google Scholar
  152. 102.
    Franceschi G, Perrone E, Alpegiani M, Bedeschi A, Della Bruna C, Zarini F (1989) In: Bentley PH, Southgate R (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, London, p 222Google Scholar
  153. 103.
    Hou D (1988) US Pat 4,767,853Google Scholar
  154. 104.
    Yoshida A, Hayashi T, Takeda N, Oida S, Ohki E (1983) Chem Pharm Bull 31: 768Google Scholar
  155. 105. (a)
    Sheehan JC, Brandt KG (1965) J Am Chem Soc 87: 5468Google Scholar
  156. 105. (b)
    Heusler K (1972) Helv Chim Acta 55: 388Google Scholar
  157. 105. (c)
    Sheehan JC, Shibahara S, Chacko E (1980) J Med Chem 23: 809Google Scholar
  158. 106.
    Crugnola A, Longo A, Casabuona F, Lombardi P (1981) Tetrahedron Lett 22: 4141Google Scholar
  159. 107.
    Ganguly AK, Girijavallabhan VM, Cavender P, Sarre O, McCombie SW (1981) US Pat 4,272,439Google Scholar
  160. 108.
    Battistini C, Foglio M, Zarini F (1982) Belg Pat 829,600Google Scholar
  161. 109.
    Brown BB, Volkmann RA (1986) Tetrahedron Lett 27: 1545Google Scholar
  162. 110.
    Giorgi R (1981) Unpublished resultsGoogle Scholar
  163. 111.
    Altamura M, Francalanci F, Marchi M (1988) Unpublished resultsGoogle Scholar
  164. 112.
    Aimetti JA, Hamanaka ES, Johnson DA, Kellogg MS (1979) Tetrahedron Lett 4631Google Scholar
  165. 113.
    Sheehan JC, Nakajima K, Chacko E (1979) Heterocycles 13: 227Google Scholar
  166. 114.
    Hungerbühler E, Lang M, Schneider P, Scartazzini R, Tosch W, Zak O (1987) 15th International Congress of Chemotherapy (Istanbul)Google Scholar
  167. 115. (a)
    Bouffard FA, Johnston DBR, Christensen BG (1980) J Org Chem 45: 1130Google Scholar
  168. 115. (b)
    Bouffard FA, Christensen BG (1981) J Org Chem 46: 2208Google Scholar
  169. 116.
    Ona H, Uyeo S, Fukao T, Doi M, Yoshida T (1985) Chem Pharm Bull 33: 4382Google Scholar
  170. 117.
    McCombie SW, Ganguly AK, Girijavallabhan VM, Jeffrey PD, Lin S, Pinto P (1981) Tetrahedron Lett 22: 3489Google Scholar
  171. 118.
    Shibasaki M, Nishida A, Ikegami S (1982) J Chem Soc Chem Commun 1324Google Scholar
  172. 119. (a)
    Osborne NF (1980) British Pat 2,036,015Google Scholar
  173. 119. (b)
    Osborne NF (1981) Eur Pat 41,768Google Scholar
  174. 120.
    Ueda Y, Martel A, Daris JP, Belleau B, Menard M (1982) Can J Chem 60: 904Google Scholar
  175. 121. (a)
    Heusler K, Woodward RB (1969) German Offenlegungsschrift 1,935,970Google Scholar
  176. 121. (b)
    Woodward RB, Heusler K, Ernest I, Burri K, Friary RJ, Haviv F, Oppolzer W, Paioni R, Syhora K, Wenger R, Whitesell JK (1977) Nouveau J Chim 1: 85Google Scholar
  177. 122.
    Lang M, Prasad K, Holick W, Gosteli J, Ernest I, Woodward RB (1979) J Am Chem Soc 101: 6296Google Scholar
  178. 123.
    Ernest I, Main AJ, Woodward RB (1981) Helv Chim Acta 64: 1303Google Scholar
  179. 124.
    Ernest I (1979) Helv Chim Acta 62: 2681Google Scholar
  180. 125.
    Longo A, Bedeschi A, Lombardi P, Gandolfi C, Franceschi G (1981) Gazz Chim Ital 111: 371Google Scholar
  181. 126.
    Sanfilippo A, Della Bruna C, Jabes D, Morvillo E, Schioppacassi G, Franceschi G, Arcamone F, Battistini C, Foglio M, Zarini F (1982) J Antibiotics 35: 1248Google Scholar
  182. 127.
    Alpegiani M, Bedeschi A, Franceschi G, Giudici F, Nannini G, Perrone E (1984) Gazz Chim Ital 114: 319Google Scholar
  183. 128.
    Miyadera T (1982) 22nd Intersci Conf Antimicrob Agents Chemother (Miami Beach), Program and Abstracts, The American Society for Microbiology, p 20Google Scholar
  184. 129.
    Lang M, Prasad K, Gosteli J, Woodward RB (1980) Helv Chim Acta 63: 1093Google Scholar
  185. 130. (a)
    Oida S, Yoshida A, Hayashi T, Takeda N, Ohki E (1980) Chem Pharm Bull 28: 3232Google Scholar
  186. 130. (b)
    Oida S, Yoshida A, Hayashi T, Takeda N, Nishimura T, Ohki E (1980) J Antibiotics 33: 107Google Scholar
  187. 131.
    Yoshida A, Hayashi T, Takeda N, Oida S, Ohki E (1981) Chem Pharm Bull 29: 1854Google Scholar
  188. 132.
    Hayashi T, Yoshida A, Takeda N, Oida S, Sugawara S, Ohki E (1981) Chem Pharm Bull 29: 3158Google Scholar
  189. 133.
    Kawamoto I, Endo R, Suzuki K, Hata T (1987) Heterocycles 25: 123Google Scholar
  190. 134.
    Corey EJ, Märkl G (1967) Tetrahedron Lett 3201Google Scholar
  191. 135.
    Cooke MD, Moore KW, Ross BC, Turner SE (1983) J Chem Soc Chem Commun 1005Google Scholar
  192. 136.
    Perrone E, Alpegiani M, Bedeschi A, Giudici F, Zarini F, Franceschi G, Della Bruna C, Jabes D, Meinardi G (1987) J Antibiotics 40: 1636Google Scholar
  193. 137.
    Alpegiani M, Perrone E (1985) Unpublished resultsGoogle Scholar
  194. 138.
    Holick W, Weis CD Unpublished results (see Ref 141)Google Scholar
  195. 139.
    Brain EG (1980) UK Pat Appl GB 2,042,508Google Scholar
  196. 140.
    Girijavallabhan VM, Ganguly AK, Liu Y-T, Pinto PA, Patel N, Hare RH, Miller GH (1986) J Antibiotics 39: 1187Google Scholar
  197. 141.
    Lang M, Schneider P, Scartazzini R, Tosch W, Konopk EA, Zak O (1987) J Antibiotics 40: 217Google Scholar
  198. 142.
    Pfaendler HR, Gosteli J, Woodward RB (1979) J Am Chem Soc 101: 6306Google Scholar
  199. 143.
    Lombardi P, Franceschi G, Arcamone F (1979) Tetrahedron Lett 3777Google Scholar
  200. 144.
    Martel A, Dextraze P, Daris J-P, Saintonge R, Lapointe P, Conway TT, Moncovic I, Kavadias G, Ueda Y, Elie P, Patil S, Caron G, Douglas JL, Menard M, Belleau B (1982) Can J Chem 60: 942Google Scholar
  201. 145.
    Longo A, Lombardi P, Gandolfi C, Franceschi G (1981) Tetrahedron Lett 22: 355Google Scholar
  202. 146.
    Lang M, Schneider P, Tosch W, Scartazzini R, Zak O (1986) J Antibiotics 39: 525Google Scholar
  203. 147.
    Capraro H-G, Francotte E, Kohler B, Rihs G, Schneider P, Scartazzini R, Zak O, Tosch W (1988) J Antibiotics 41: 759Google Scholar
  204. 148.
    Bedeschi A, Visentin G, Perrone E, Zarini F, Franceschi G, Meinardi G, Castellani P, Jabes D, Della Bruna C (1988) 28th Intersci Conf Antimicrob Agents Chemother (Los Angeles), Program and Abstracts, The American Society for Microbiology, p 149Google Scholar
  205. 149.
    Bedeschi A, Visentin G, Perrone E, Zarini F, Franceschi G, Meinardi G, Castellani P, Jabes D, Rossi R, Della Bruna C (1990) J Antibiotics 43: 306Google Scholar
  206. 150. (a)
    Della Bruna C, Jabes D, Castellani P, Rossi R, Meinardi G, Alpegiani M, Zarini F, Perrone E, Franceschi G (1988) 28th Intersci Conf Antimicrob Agents Chemother (Los Angeles), Program and Abstracts, The American Society for Microbiology, p 149Google Scholar
  207. 150. (b)
    Alpegiani M, Bedeschi A, Giudici F, Perrone E, Visentin G, Zarini F, Franceschi G (1990) Heterocycles 31: (in press)Google Scholar
  208. 151.
    DiNinno F, Muthard DA, Ratcliffe RW, Christensen BG (1982) Tetrahedron Lett 23: 3535Google Scholar
  209. 152.
    Fontana E, Alpegiani M, Perrone E, Vicario GP (1987) J Labelled Compd Radiopharm 24: 41Google Scholar
  210. 153.
    Alpegiani M, Bedeschi A, Perrone E, Franceschi G (1984) Tetrahedron Lett 25: 4171Google Scholar
  211. 154.
    Kukolja S, Lammert SR, Gleissner MRB, Ellis AI (1976) J Am Chem Soc 98: 5040Google Scholar
  212. 155.
    Yanagisawa H, Ando A (1982) Tetrahedron Lett 23: 3379Google Scholar
  213. 156. (a)
    Afonso A, Hon F, Weinstein J, Ganguly AK (1982) J Am Chem Soc 104: 6138Google Scholar
  214. 156. (b)
    Afonso A, Hon F (1982) US Pat 4,347,183Google Scholar
  215. 157.
    Afonso A, Ganguly AK, Girijavallabhan VM, McCombie S (1985) In: Brown AG, Roberts SM (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics The Royal Society of Chemistry, Special Publication No 52, London, p 266Google Scholar
  216. 158.
    Yoshida A, Hayashi T, Takeda N, Oida S, Ohki E (1983) Chem Pharm Bull 31: 768Google Scholar
  217. 159.
    Bordner J, English A, Foulds G, Girard A, Gootz T, Jasys J, Kelbaugh P, Kellogg M, Hamanaka E, Lindner D, Retsema J, Volkmann R, Campbell B (1988) 28th Intersci Conf Antimicrob Agents Chemother (Los Angeles), Program and Abstracts, The American Society for Microbiology, p 148Google Scholar
  218. 160.
    Krahmer-Seifert U, Emmer G (1984) Heterocycles 22: 375Google Scholar
  219. 161.
    Cue BW, Pirie DK (1988) Eur Pat Appl 283,253Google Scholar
  220. 162. (a)
    Yoshida A, Tajima Y, Takeda N, Oida S (1984) Tetrahedron Lett 25: 2793Google Scholar
  221. 162. (b)
    Shibata T, Sugimura Y (1989) J Antibiotics 42: 374Google Scholar
  222. 163.
    McCombie SW, Metz WA, Afonso A (1986) Tetrahedron Lett 27: 305Google Scholar
  223. 164.
    Franceschi G, Perrone E, Alpegiani M, Bedeschi A, Battistini C, Zarini F, Della Bruna C (1989) J Antimicrob Chemother 23 (Suppl C): 1Google Scholar
  224. 165.
    Altamura M, Cesti P, Francalanci F, Marchi M, Cambiaghi F (1989) J Chem Soc Perkin Trans 1 1225Google Scholar
  225. 166.
    Lang M, Hungerbühler E, Schneider P, Scartazzini R, Tosch W, Zak O (1986) 26th Intersci Conf Antimicrob Agents Chemother (New Orleans), Program and Abstracts, The American Society for Microbiology, p 329Google Scholar
  226. 167.
    Battistini C, Vioglio S, Scarafile C, Franceschi G (1985) Heterocycles 23: 1929Google Scholar
  227. 168.
    Alpegiani M, Zarini F, Perrone E (1989) 1er Congreso Conjuncto Hispano-Italiano de Quimica Terapeutica (Granada), Program and Abstracts, p 318Google Scholar
  228. 169. (a)
    Ishiguro M, Iwata H, Nakatsuka T, Tanaka R, Maeda Y, Nishihara T, Noguchi T, Nishino T (1986) 26th Intersci Conf Antimicrob Agents Chemother (New Orleans), Program and Abstracts, The American Society for Microbiology, p 329Google Scholar
  229. 169. (b)
    Ishiguro M, Iwata H, Tanaka R (1988) Eur Pat Appl 273,747Google Scholar
  230. 169. (c)
    Ishiguro M, Iwata H, Nakatsuka T, Tanaka R, Maeda Y, Nishihara T, Noguchi T, Nishino T (1988) J Antibiotics 41: 1685Google Scholar
  231. 170.
    Ananda GDS, Stoodley RJ (1985) Tetrahedron Lett 26: 497Google Scholar
  232. 171.
    Barker AJ, Jenkins MJ (1989) In: Bentley PH, Southgate R (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 70, London, p 259Google Scholar
  233. 172.
    Marchand-Brynaert J, Vekemans J, Bogdan S, Cossement M, Ghosez L (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 269Google Scholar
  234. 173.
    Cossement M, Marchand-Brynaert J, Bogdan S, Ghosez L (1983) Tetrahedron Lett 24: 2563Google Scholar
  235. 174.
    Girijavallabhan VM, Ganguly AK, Pinto P, Versace R (1983) Tetrahedron Lett 24: 3179Google Scholar
  236. 175.
    Girijavallabhan VM, Ganguly AK, Pinto PA, Versace RW, Patel N, Hare RR, Miller GH (1986) J Antibiotics 39: 1182Google Scholar
  237. 176.
    Gala D, Steinman M, Jaret RS (1986) J Org Chem 51: 4488Google Scholar
  238. 177.
    Girijavallabhan VM, Ganguly AK, Pinto P, Versace R (1983) J Chem Soc Chem Commun 908Google Scholar
  239. 178.
    Shibuya M, Kubota S (1980) Tetrahedron Lett 21: 4009Google Scholar
  240. 179.
    Kim CU, Misco PF, McGregor DN (1982) J Org Chem 47: 171Google Scholar
  241. 180.
    Brighty KE (1988) US Pat 4,782,146Google Scholar
  242. 181.
    Brighty KE, Lindner DL (1988) US Pat 4,782,145Google Scholar
  243. 182.
    Kametani T, Chu S-D, Itoh A, Wang T-C, Nakayama A, Honda T (1988) J Chem Soc Chem Commun 544Google Scholar
  244. 183. (a)
    DiNinno F, Linek EV, Christensen BG (1979) J Am Chem Soc 101: 3210Google Scholar
  245. 183. (b)
    Christensen BG, DiNinno F (1979) US Pat 4,168,314Google Scholar
  246. 184.
    Oida S, Yoshida A, Hayashi T, Nakayama E, Sato S, Ohki E (1980) Tetrahedron Lett 21: 619Google Scholar
  247. 185.
    Joyeau R, Kobaiter R, Sadet J, Wakselman M (1989) Tetrahedron Lett 30: 337Google Scholar
  248. 186.
    Salzmann TN, Christensen BG (1980) Tetrahedron Lett 21: 31Google Scholar
  249. 187.
    Marchand-Brynaert J, Ghosez L (1980) Tetrahedron Lett 21: 3085Google Scholar
  250. 188. (a)
    Bissolino P, Alpegiani M, Bedeschi A, Perrone E, Zarini F (1987) 17° Convegno Nazionale della Divisione di Chimica Organica (Fiuggi), Società Chimica Italiana, Program and Abstracts, p 209Google Scholar
  251. 188. (b)
    Barth WE (1980) Eur Pat Appl 8,917Google Scholar
  252. 189.
    Wasserman HH, Han WT (1985) J Am Chem Soc 107: 1444Google Scholar
  253. 190. (a)
    Cherry PC, Newall CE, Watson NS (1979) J Chem Soc Chem Commun 663Google Scholar
  254. 190. (b)
    Newall CE (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 151Google Scholar
  255. 191.
    Beels CD, Abu Rabie MS, Murray-Rust P, Murray-Rust J (1979) J Chem Soc Chem Commun 665Google Scholar
  256. 192.
    Betty S, Davies HG, Kitchin J (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 347Google Scholar
  257. 193.
    Foxton MW, Newall CE, Ward P (1981) In: Gregory GI (ed) Recent Advances in the Chemistry of β-Lactam Antibiotics, The Royal Society of Chemistry, Special Publication No 38, London, p 281Google Scholar
  258. 194. (a)
    Eglington AJ (1977) J Chem Soc Chem Commun 720Google Scholar
  259. 194. (b)
    Bentley PH, Brooks G, Gilpin ML, Hunt E (1977) J Chem Soc Chem Commun 905Google Scholar
  260. 195.
    Banville J, Lapointe P, Belleau B, Menard M (1988) Can J Chem 66: 1390Google Scholar
  261. 196. (a)
    Maky Y, Mitsumori N, Sako M, Suzuki M (1981) J Chem Soc Perkin Trans 1 2087Google Scholar
  262. 196. (b)
    Prasad K, Schulz G, Hamberger H, Stütz P (1982) Heterocycles 19: 291Google Scholar
  263. 197. (a)
    Tanaka T, Hashimoto T, Lino K, Sugimura Y, Miyadera T (1982) Tetrahedron Lett 23: 1075Google Scholar
  264. 197. (b)
    Tanaka T, Hashimoto T, lino K, Sugimura Y, Miyadera T (1982) J Chem Soc Chem Commun 713Google Scholar
  265. 198.
    Daniels N, Johnson G, Ross BC (1983) J Chem Soc Chem Commun 1006Google Scholar
  266. 199.
    Cooke MD, Moore KW, Barker AJ, Teall MR, Walmsley JG, Coomber JD (1986) 26th Intersci Conf Antimicrob Agents Chemother (New Orleans), Program and Abstracts, The American Society for Microbiology, p 330Google Scholar
  267. 200.
    Cooke MD, Moore KW, Ross BC, Turner SE (1985) In: Brown AG, Roberts SM (eds) Recent Advances in the Chemistry of β-Lactam Antibiotics The Royal Society of Chemistry, Special Publication No 52, London, p 100Google Scholar
  268. 201.
    Alpegiani M, Bedeschi A, Perrone E, Franceschi G (1986) Tetrahedron Lett 27: 3041Google Scholar
  269. 202.
    Barker AJ, Teall MR, Johnson G (1987) Tetrahedron Lett 28: 2283Google Scholar
  270. 203.
    Alpegiani M, Bedeschi A, Perrone E (1982) Unpublished resultsGoogle Scholar
  271. 204. (a)
    Wolfe S, Bassett RN, Caldwell SM, Wasson FI (1969) J Am Chem Soc 91: 7205Google Scholar
  272. 204. (b)
    Lattrell R (1974) Liebigs Ann Chem 1937Google Scholar
  273. 204. (c)
    Bachi MD, Goldberg O (1974) J Chem Soc Perkin Trans 1 1184Google Scholar
  274. 205. (a)
    Baldwin JE (1976) J Chem Soc Chem Commun 734Google Scholar
  275. 205. (b)
    Baldwin JE, Cutting J, Dupont W, Kruse L, Silberman L, Thomas RC (1976) J Chem Soc Chem Commun 736Google Scholar
  276. 206.
    Arrowsmith JE, Greengrass CW (1982) Tetrahedron Lett 23: 357Google Scholar
  277. 207.
    Ghosez L, Marchand-Brynaert J, Vekemans J, Bogdan S (1983) Tetrahedron 39: 2493Google Scholar
  278. 208.
    Henderson A, Johnson G, Moore KW, Ross BC (1982) J Chem Soc Chem Commun 809Google Scholar
  279. 209.
    Perrone E, Alpegiani M, Bedeschi A, Foglio M, Franceschi G (1983) Tetrahedron Lett 24:1631Google Scholar
  280. 210.
    Franceschi G, Alpegiani M, Battistini C, Bedeschi A, Perrone E, Zarini F (1987) Pure & Appl Chemistry 59: 467Google Scholar
  281. 211.
    Perrone E, Alpegiani M, Battaglia R, Bedeschi A, Franceschi G (1985) in: Brown AG, Roberts SM eds Recent Advances in the Chemistry of β-Lactam Antibiotics The Royal Society of Chemistry, Special Publication No 52, London, 361Google Scholar
  282. 212.
    Battaglia R, Alpegiani M, Perrone E, Vicario GP (1987) Gazz Chim Ital 117: 1Google Scholar
  283. 213.
    Alpegiani M, Bedeschi A, Perrone E, Franceschi G (1984) Tetrahedron Lett 25: 4167Google Scholar
  284. 214.
    Perrone E, Alpegiani M, Bedeschi A, Giudici F, Foglio M, Franceschi G (1983) Tetrahedron Lett 24: 3283Google Scholar
  285. 215.
    Perrone E, Alpegiani M, Bedeschi A, Giudici F, Zarini F, Franceschi G, Della Bruna C, Jabes D, Meinardi G (1986) J Antibiotics 39: 1351Google Scholar
  286. 216.
    Daniels NJ, Johnson G, Ross BC, Yeomans MA (1982) J Chem Soc Chem Commun 1119Google Scholar
  287. 217.
    Cooke MD, Moore KW, Ross BC, Turner SE (1983) Tetrahedron Lett 24: 3373Google Scholar
  288. 218.
    Perrone E, Alpegiani M, Bedeschi A, Borghi D, Giudici F, Franceschi G (1986) J Org Chem 51: 3413Google Scholar
  289. 219.
    Freeman F (1984) Chem Rev 84: 117Google Scholar
  290. 220.
    Baldwin JE, Forrest AK, Ko S, Sheppard LN (1987) J Chem Soc Chem Commun 81Google Scholar
  291. 221.
    Nagao Y, Kumagai T, Takao S, Hagiwara Y, Abe T, Ochiai M, Fujita E, Taga T, Aoyagi S, Nagase Y, Inoue Y (1985) 17th Congress of Heterocyclic Chemistry (Sapporo), Abstracts of Papers, p 128Google Scholar
  292. 222.
    Douglas JL, Martel A, Caron G, Menard M, Silveira L, Clardy J (1984) Can J Chem 62: 2282Google Scholar
  293. 223.
    Girijavallabhan VM, McCombie SW, Pinto P, Liu S-I, Versace R (1987) J Chem Soc Chem Commun 691Google Scholar
  294. 224.
    Kawamoto I, Endo R, Sugawara S (1986) J Antibiotics 39: 1551Google Scholar
  295. 225.
    Emmer G, Kneussel P, Hildebrandt J, Turnowsky F, Haselberg A, Wenzel A, Stütz P (1985) J Antibiotics 38: 1371Google Scholar
  296. 226.
    Osborne NF (1982) J Chem Soc Perkin Trans 1 1429Google Scholar
  297. 227.
    Cherry PC, Evans DN, Newall CE, Watson NS, Murray-Rust P, Murray-Rust J (1980) Tetrahedron Lett 21: 561Google Scholar
  298. 228.
    Alpegiani M, Bedeschi A, Perrone E, Zarini F, Franceschi G (1985) Heterocycles 23: 2255Google Scholar
  299. 229.
    Alpegiani M, Bedeschi A, Perrone E, Zarini F, Franceschi G (1988) Heterocycles 27: 1329Google Scholar
  300. 230.
    Alpegiani M, Perrone E, Franceschi G (1988) Heterocycles 27: 49Google Scholar
  301. 231.
    Franceschi G, Perrone E (1987) In: Umezawa H (ed) Frontiers of Antibiotic Research, Academic New York, p 227Google Scholar
  302. 232.
    Oida S, Yoshida A, Hayashi T, Takeda N, Ohki F (1980) Chem Pharm Bull 28: 3258Google Scholar
  303. 233.
    Ganguly AK, Afonso A, Girijavallabhan VM, McCombie SW (1984) 24th Intersci Conf Antimicrob Agents Chemother (Washington), Program and Abstracts, The American Society for Microbiology, p 218Google Scholar
  304. 234.
    Alpegiani M, Bedeschi A, Foglio M, Perrone E (1984) Gazz Chim Ital 114: 393Google Scholar
  305. 235.
    Jeffrey PD, McCombie SW (1982) J Org Chem 47: 587Google Scholar
  306. 236.
    Deziel R (1987) Tetrahedron Lett 28: 4371Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1990

Authors and Affiliations

  • Ettore Perrone
    • 1
  • Giovanni Franceschi
    • 1
  1. 1.Infectious Diseases Dept.Farmitalia-Carlo ErbaMilanoItaly

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