Skip to main content

Part of the book series: Springer Theses ((Springer Theses))

  • 515 Accesses

Abstract

Plakortide E (85) and plakortone B (87) were first isolated from the Jamaican marine sponge Plakortis halichondrioides along with plakortones A, C, D in 1996 by Patil and coworkers. In 1999, plakortone B (87) was also isolated from the Caribbean sponge Plakortis simplex along with plakortones C–F by Fattorusso and coworkers. In their continuing program to identify compounds with antifungal properties, Wright and coworkers also isolated a molecule identified as plakortide E (85) from the sponge Plakortis halichondrioides in 2002.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Patil AD, Freyer AJ, Bean MF, Carte BK, Westley JW, Johnson RK, Lahouratate P (1996) Tetrahedron 52:377–394

    Article  CAS  Google Scholar 

  2. Caffierei F, Fattorusso E, Taglialatela-Scafati O, Di Rosa M, Ianaro A (1999) Tetrahedron 55:13831–13840

    Article  Google Scholar 

  3. Chen Y, McCarthy PJ, Harmody DK, Schimoler-O’Rourke R, Chilson K, Selitrennikoff C, Pomponi SA, Wright AE (2002) J Nat Prod 65:1509–1512

    Article  CAS  Google Scholar 

  4. Semmelhack MF, Hooley RJ, Kraml CK (2006) Org Lett 8:5203–5206

    Article  CAS  Google Scholar 

  5. Xie X-G, Wu X-W, Lee H-K, Peng X-S, Wong HNC (2010) Chem Eur J 16:6933–6941

    Article  CAS  Google Scholar 

  6. Zhao Q (2006) PhD thesis, Shanghai institute of organic chemistry, the Chinese Academy of Science

    Google Scholar 

  7. Negishi E, Valente LF, Kobayashi MJ (1980) Am Chem Soc 102:3298–3299

    Article  CAS  Google Scholar 

  8. Smith AB III, Beauchamp TJ, LaMarche MJ, Kaufman MD, Qiu Y, Arimoto H, Jones DR, Kobayashi K (2000) J Am Chem Soc 122:8654–8664

    Article  CAS  Google Scholar 

  9. Smith AB III, Kaufman MD, Beauchamp TJ, LaMarche MJ, Arimoto H (1999) Org Lett 1:1823–1826

    Article  CAS  Google Scholar 

  10. Dutheuil G, Webster MP, Worthington PA, Aggarwal VK (2009) Angew Chem Int Ed 48:1–4

    Google Scholar 

  11. Leopold H, Hoffmann HMR, Wippel HG (1958) Chem Ber 91:61–63

    Article  Google Scholar 

  12. Wadsworth WS Jr, Emmons WD (1961) J Am Chem Soc 83:1733–1738

    Article  CAS  Google Scholar 

  13. Maryanoff BE, Reitz AB (1989) Chem Rev 89:863–927

    Article  CAS  Google Scholar 

  14. Gotor-Fernández V, Brieva R, Gotor V (2006) J Mol Catal B Enzym 40:111–120

    Article  Google Scholar 

  15. Ghanem A (2007) Tetrahedron 63:1721–1754

    Article  CAS  Google Scholar 

  16. Feldman KS, Pravez M (1986) J Am Chem Soc 108:1328–1330

    Article  CAS  Google Scholar 

  17. Feldman KS, Simpson RE (1989) J Am Chem Soc 111:4878–4886

    Article  CAS  Google Scholar 

  18. Feldman KS, Kraebel CM (1992) J Org Chem 57:4574–4576

    Article  CAS  Google Scholar 

  19. Weinreb CK, Hartsough D, Feldman KS (1995) Tetrahed Lett 36:6859–6862

    CAS  Google Scholar 

  20. Zhao Q, Wong HNC (2007) Tetrahedron 63:6296–6305

    Article  CAS  Google Scholar 

  21. McCoy LL (1958) J Am Chem Soc 80:6568–6572

    Article  CAS  Google Scholar 

  22. McCoy LL (1960) J Org Chem 25:2078–2082

    Article  CAS  Google Scholar 

  23. McCoy LL (1962) J Am Chem Soc 84:2246–2249

    Article  Google Scholar 

  24. Bottini AT (1963) J Org Chem 28:157–160

    Google Scholar 

  25. Chenault HK, Kim M-J, Akiyama A, Miyazawa T, Simon ES, Whitesides GM (1987) J Org Chem 52:2608–2611

    Article  CAS  Google Scholar 

  26. Barton P, Law AP, Page MI (1994) J Chem Soc Perkin Trans 2:2021–2029

    Google Scholar 

  27. Borszeky K, Mallat T, Baiker A (1997) Tetrahed Asymm 8:3745–3753

    Article  CAS  Google Scholar 

  28. Murahashi S-I, Naota T, Kuwabara T, Saito T, Kumobayashi H, Akutagawalb S (1990) J Am Chem Soc 112:7820–7822

    Article  CAS  Google Scholar 

  29. Yoshida M, Miura M, Nojima M, Kusabayashi S (1983) J Am Chem Soc 105:6279–6285

    Article  CAS  Google Scholar 

  30. Ito T, Tokuyasu T, Masuyama A, Nojima M, McCullough KJ (2003) Tetrahedron 59:525–536

    Article  CAS  Google Scholar 

  31. Tokuyasu T, Kunikawa S, McCullough KJ, Masuyama A, Nojima M (2005) J Org Chem 70:251–260

    Article  CAS  Google Scholar 

  32. Isayama S (1990) Bull Chem Soc Jpn 63:1305–1310

    Article  CAS  Google Scholar 

  33. Isayama S, Mukaiyama T (1989) Chem Lett 18:573–576

    Article  Google Scholar 

  34. O’Neill PM, Pugh M, Davies J, Ward SA, Park BK (2001) Tetrahed Lett 42:4569–4571

    Article  Google Scholar 

  35. Yu J-Q, Corey EJ (2002) Org Lett 4:2727–2730

    Article  CAS  Google Scholar 

  36. Harris JR, Waetzig SR, Woerpel KA (2009) Org Lett 11:3290–3293

    Article  CAS  Google Scholar 

  37. Parsons AT, Campbell MJ, Johnson JS (2008) Org Lett 10:2541–2544

    Article  CAS  Google Scholar 

  38. Stahl SS (2004) Angew Chem Int Ed 43:3400–3420

    Article  CAS  Google Scholar 

  39. Baldwin AC (1983) In: Patai S (ed) The chemistry of peroxides, vol 1. Wiley, Chichester, pp 97–104

    Google Scholar 

  40. Korshin EE, Bachi MD (2006) In: Rappoport Z (ed) The chemistry of peroxides, vol 2. Wiley, Chichester, pp 189–305

    Google Scholar 

  41. Horner L, Hoffmann HMR, Wippel HG, Klahre G (1959) Chem Ber 92:2499–2505

    Article  CAS  Google Scholar 

  42. Schwartz J, Labinger JA (1976) Angew Chem Int Ed Engl 15:333–340

    Article  Google Scholar 

  43. Colvin EW, Hamill BJ (1973) J Chem Soc Chem Commun:151–152

    Google Scholar 

  44. Colvin EW, Hamill BJ (1977) J Chem Soc Chem Perkin Trans 1:869–874

    Google Scholar 

  45. Seyferth D, Hilbert P, Marmor RS (1970) Tetrahed Lett 11:2493–2496

    Article  Google Scholar 

  46. Gilbert JC, Weerasooriya U (1982) J Org Chem 47:1837–1845

    Article  CAS  Google Scholar 

  47. Gilbert JC, Weerasooriya U (1979) J Org Chem 44:4997–4998

    Article  CAS  Google Scholar 

  48. Ohira S (1989) Synth Commun 19:561–564

    Article  CAS  Google Scholar 

  49. Müller S, Liepold B, Roth GJ, Bestmann HJ (1996) Synlett:521–522

    Google Scholar 

  50. Corey EJ, Fuchs PL (1972) Tetrahed Lett 13:3769–3772

    Article  Google Scholar 

  51. Desai NB, McKelvie N (1962) J Am Chem Soc 84:1745–1747

    Article  Google Scholar 

  52. Marjanovic J, Kozmin SA (2007) Angew Chem Int Ed 46:8854–8857

    Article  CAS  Google Scholar 

  53. Lerm M, Gais H-J, Cheng K, Vermeeren C (2003) J Am Chem Soc 125:9653–9667

    Article  CAS  Google Scholar 

  54. Wailes PC, Weigold HJ (1970) Organomet Chem 24:405–411

    Article  CAS  Google Scholar 

  55. Hart DW, Schwartz J (1974) J Am Chem Soc 96:8115–8116

    Article  CAS  Google Scholar 

  56. Sun RC, Okabe M, Coffen DL, Schwartz J (1998) Org Synth 9:640

    CAS  Google Scholar 

  57. Nicolaou KC, Li Y, Fylaktakidou KC, Mitchell HJ, Sugita K (2001) Angew Chem Int Ed 40:3854–3857

    Article  CAS  Google Scholar 

  58. Zhang H, Guibe F, Balavoine G (1990) J Org Chem 55:1857–1867

    Article  CAS  Google Scholar 

  59. Betzer JF, Le Menez P, Prunet J, Brion J-D, Ardisson J, Pancrazi A (2002) Synlett:1–15

    Google Scholar 

  60. Semmelhack MF, Hooley RJ (2003) Tetrahed Lett 44:5737–5739

    Article  CAS  Google Scholar 

  61. Panek JS, Jain NF (2001) J Org Chem 66:2747–2756

    Article  CAS  Google Scholar 

  62. Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed 44:4442–4489

    Article  CAS  Google Scholar 

  63. Diederich F, Stang PJ (1998) Metal-catalyzed cross-coupling reactions, 1st edn. Wiley-VCH, Weinheim

    Book  Google Scholar 

  64. de Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley-VCH, Weinheim

    Book  Google Scholar 

  65. King AO, Okukado N, Negishi E (1977) J Chem Soc Chem Commun 19:683–684

    Article  Google Scholar 

  66. Zeng F, Negishi E (2001) Org Lett 3:719–722

    Article  CAS  Google Scholar 

  67. Knochel P, Singer RD (1993) Chem Rev 93:2117–2188

    Article  CAS  Google Scholar 

  68. Boudier A, Bromm LO, Lotz M, Knochel P (2000) Angew Chem Int Ed 39:4414–4435

    Article  Google Scholar 

  69. Dussault PH, Eary CT (1998) J Am Chem Soc 120:7133–7134

    Article  CAS  Google Scholar 

  70. Xu C, Raible JM, Dussault PH (2005) Org Lett 7:2509–2511

    Article  CAS  Google Scholar 

  71. Evans DA, Chapman KT, Huang DT, Kawaguchi AT (1987) Angew Chem Int Ed Engl 26:1184–1186

    Article  Google Scholar 

  72. Evans DA, Urpi F, Somers TC, Clark JS, Bilodeau MT (1990) J Am Chem Soc 112:8215–8216

    Article  CAS  Google Scholar 

  73. Ihara M, Katsumata A, Setsu F, Tokunaga Y, Fukumoto K (1996) J Org Chem 61:677–684

    Article  CAS  Google Scholar 

  74. Neumann CS, Walsh CT (2008) J Am Chem Soc 130:14022–14023

    Article  CAS  Google Scholar 

  75. af Gennäs GB, Talman V, Aitio O, Ekokoski E, Finel M, Tuominen RK, Yli-Kauhaluoma J (2009) J Med Chem 52:3969–3981

    Article  Google Scholar 

  76. Ihara M, Setsu F, Shohda M, Taniguchi N, Tokunaga Y, Fukumoto K (1994) J Org Chem 59:5317–5323

    Article  CAS  Google Scholar 

  77. Ihara M, Takahashi M, Taniguchi M, Fukumoto K, Kametani T (1987) J Chem Soc Chem Commun:619–620

    Google Scholar 

  78. Neises B, Steglich W (1978) Angew Chem Int Ed Engl 90:556–557

    Article  CAS  Google Scholar 

  79. Kogen H, Tomioka K, Hashimoto S, Koga K (1981) Tetrahedron 37:3951–3956

    Article  CAS  Google Scholar 

  80. Czernecki S, Georgoulis C, Provelenghiou C (1976) Tetrahed Lett 17:3535–3536

    Article  Google Scholar 

  81. Kuhn R, Löw L, Trishmann H (1957) Chem. Ber. 90:203

    Article  CAS  Google Scholar 

  82. Fukuzawa A, Sato H, Masamune T (1987) Tetrahed Lett 28:4303–4306

    Google Scholar 

  83. Roberston DE, Bornscheuer UT (2005) Curr Opin Chem Biol 9:164–165

    Article  Google Scholar 

  84. Beisson F, Tiss A, Riviere C, Verger R (2000) Eur J Lipid Sci Technol 102:133–153

    Article  CAS  Google Scholar 

  85. Schoffers E, Golebioeski A, Johnson CR (1996) Tetrahedron 52:3769–3826

    Article  CAS  Google Scholar 

  86. Klibanov AM (1997) Trends Biotechnol 15:87–101

    Article  Google Scholar 

  87. Faber K (1997) Biotransformation in organic chemistry, 3rd edn. Springer, Heidelberg

    Google Scholar 

  88. Schmid RD, Verger R (1998) Angew Chem Int Ed 37:1608–1633

    Article  Google Scholar 

  89. Haraldsson G (1992) The application of lipases in organic synthesis. In: Patai S (ed) The chemistry of acid derivatives, vol 2. Wiley, Chichester, pp 1395–1473

    Chapter  Google Scholar 

  90. Wong C-H, Whitesides GM (1994) Enzymes in synthetic organic chemistry. Pergamon, Oxford

    Google Scholar 

  91. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Nature 409:258–268

    Article  CAS  Google Scholar 

  92. Moss GP (1996) Pure Appl Chem 68:2193–2222

    Article  CAS  Google Scholar 

  93. Sakai T, Kawabata I, Kishimoto T, Ema T, Utaka M (1997) J Org Chem 62:4906–4907

    Article  CAS  Google Scholar 

  94. Sakai T, Liu Y, Ohta H, Korenaga T, Ema T (2005) J Org Chem 70:1369–1375

    Article  CAS  Google Scholar 

  95. Andrade LH, Barcellos T (2009) Org Lett 11:3052–3055

    Article  CAS  Google Scholar 

  96. Shing TKM, Tsui H-C, Zhou Z-H (1995) J Org Chem 60:3121–3130

    Article  CAS  Google Scholar 

  97. Yu P, Yang Y, Zhang Z-Y, Mak TCW, Wong HNC (1997) J Org Chem 62:6359–6366

    Article  CAS  Google Scholar 

  98. Peng XS, Wong HNC (2006) Chem Asian J 1:111–120

    Article  CAS  Google Scholar 

  99. Peng XS (2006) PhD thesis, the Chinese University of Hong Kong, Hong Kong

    Google Scholar 

  100. Lee JS, Fuchs PL (2005) J Am Chem Soc 127:13122–13123

    Article  CAS  Google Scholar 

  101. Grondal C, Jeanty M, Jeanty M (2010) Nat Chem 2:167–178

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Sun, XY. (2012). Results and Discussion. In: Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27195-3_2

Download citation

Publish with us

Policies and ethics