Skip to main content
SpringerLink
Log in

Synthesis of Saturated Six-Membered Ring Lactones

  • Chapter
  • First Online:
Synthesis of Saturated Oxygenated Heterocycles I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 35))

Abstract

The δ-lactone moiety is a common structural framework found in many natural products that exhibit interesting biological properties. This review details a collection of various selected methods developed for the synthesis of saturated δ-lactones. Synthesis of unsaturated δ-lactones and manipulation thereof to saturated δ-lactones are not covered in this review.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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. Rasmussen JK (1977) Synthesis: 91

    Google Scholar 

  2. Reetz MT (1982) Angew Chem Int Ed 21:96

    Google Scholar 

  3. Rocca JR, Tumlinson JH, Glancey BM, Lofren CS (1983) Tetrahedron Lett 24:1889

    CAS  Google Scholar 

  4. Gunasekara SP, Longley RE, Schulte GK (1991) J Org Chem 56:1346

    Google Scholar 

  5. Endo A, Kuroda M, Tsujita M (1976) J Antibiot 29:1346

    CAS  Google Scholar 

  6. Barua NC, Schmidt RR (1986) Synthesis: 1067

    Google Scholar 

  7. Thompson CM (1987) Tetrahedron Lett 28:4243

    CAS  Google Scholar 

  8. Mori K (1989) Tetrahedron 45:3233

    CAS  Google Scholar 

  9. Boucard V, Broustal G, Campagne JM (2007) Eur J Org Chem: 225

    Google Scholar 

  10. Florence GJ, Gardner NM, Paterson I (2008) Nat Prod Rep 25:342

    CAS  Google Scholar 

  11. Chiu P, Leung LT, Ko CBB (2010) Nat Prod Rep 27:1066

    CAS  Google Scholar 

  12. Schreiber SL (1991) Science 251:283

    CAS  Google Scholar 

  13. Rosen MK, Schreiber SL (1992) Angew Chem Int Ed 31:384

    Google Scholar 

  14. Endo A (1979) J Antibiot 32:854

    Google Scholar 

  15. Alberts AW, Chen J, Kuron G, Hunt V, Huff J, Hoffman CH, Rothrock J, Lopez M, Joshua H, Harris E, Patchett AA, Monaghan R, Currie S, Stapley E, Albers-Schönberg G, Hensens O, Hirschfield J, Hoogsteen K, Liesch J (1980) Proc Natl Acad Sci USA 77:3957

    CAS  Google Scholar 

  16. Endo A, Kuroda M, Tsujita Y (1976) J Antibiot 26:1346

    Google Scholar 

  17. Brown AG, Smale TC, King TJ, Hasenkamp R, Thompson RH (1976) J Chem Soc Perkin 1: 1165

    Google Scholar 

  18. Anliker R, Dvornik D, Gubler K, Heusser H, Prelog V (1956) Helv Chim Acta 39:1785

    CAS  Google Scholar 

  19. Djerassi C, Zderic JA (1956) J Am Chem Soc 78:6390

    CAS  Google Scholar 

  20. Li ZL, Pan DJ, Hu CQ, Wu QL, Yang SS, Xu GY (1982) Acta Chimi Sin 40:447

    CAS  Google Scholar 

  21. Li ZL, Pan DJ, Wu QL, Xu GY (1982) Acta Chimi Sin 40:757

    CAS  Google Scholar 

  22. Zhou BN, Ying B, Song GQ, Chen ZX, Han J, Yan YF (1983) Planta Med 47:35

    CAS  Google Scholar 

  23. Hamburger M, Shieh H, Pezzuto J, Cordell GA, Zhou BN (1988) Planta Med 54:579

    CAS  Google Scholar 

  24. Hamburger MO, Shieh HL, Zhou BN, Pezzuto JM, Cordell GA (1989) Magn Reson Chem 27:1025

    CAS  Google Scholar 

  25. Akdemir Z, Calis I, Junior P (1991) Planta Med 57:584

    CAS  Google Scholar 

  26. Ono M, Ito Y, Kubo S, Nohara T (1997) Chem Pharm Bull 45:1094

    CAS  Google Scholar 

  27. Wurzel G, Becker H, Eicher T, Tiefensee K (1990) Planta Med 56:444

    CAS  Google Scholar 

  28. Wurzel G, Becker H (1990) Phytochemistry 29:2565

    CAS  Google Scholar 

  29. Zinsmeister HD, Becker H, Eicher T (1991) Angew Chem Int Ed 30:130

    Google Scholar 

  30. Thiel R, Adam KP, Zapp J, Becker H (1997) Pharm Pharmacol Lett 7:103

    CAS  Google Scholar 

  31. Lakner FJ, Hager LP (1996) J Org Chem 61:3923

    CAS  Google Scholar 

  32. Takano S, Shimazaki Y, Iwabuchi Y, Ogasawara K (1990) Tetrahedron Lett 31:3619

    CAS  Google Scholar 

  33. Ikan R, Gottlieb R, Bergmann ED, Ishay J (1969) J Insect Physiol 15:1709

    CAS  Google Scholar 

  34. Schulz S, Nishida R (1996) Bioorg Med Chem 4:341

    CAS  Google Scholar 

  35. Crouse GD, Sparks TC (1998) Rev Toxicol 2:133

    CAS  Google Scholar 

  36. Martin CJ, Timoney MC, Sheridan RM, Kendrew SG, Wilkinson B, Staunton J, Leadlay PF (2003) Org Biomol Chem 1:4144

    CAS  Google Scholar 

  37. Pappo R, Jung CJ (1962) Tetrahedron Lett 3:365

    Google Scholar 

  38. Chavdarian CG, Heathcock CH (1975) J Org Chem 40:2970

    CAS  Google Scholar 

  39. Coke JL, Richon AB (1976) J Org Chem 41:3516

    CAS  Google Scholar 

  40. Khan HA, Paterson I (1982) Tetrahedron Lett 23:5083

    CAS  Google Scholar 

  41. Yamaguchi M, Shibato K, Hirao I (1984) Tetrahedron Lett 25:1159

    CAS  Google Scholar 

  42. Gerth DB, Giese B (1986) J Org Chem 51:3726

    CAS  Google Scholar 

  43. Sakamoto A, Yamamoto Y, Oda J (1987) J Am Chem Soc 109:7188

    CAS  Google Scholar 

  44. Priestap HA, Bonafede JD, Rúveda EA (1977) Phytochemistry 16:1579

    CAS  Google Scholar 

  45. Carretero JC, Ghosez L (1988) Tetrahedron Lett 29:2059

    CAS  Google Scholar 

  46. White JD, Jayasinghe LR (1988) Tetrahedron Lett 29:2139

    CAS  Google Scholar 

  47. Reddy GB, Minami T, Hanamoto T, Hiyama T (1991) J Org Chem 56:5752

    CAS  Google Scholar 

  48. Shimada S, Tohno I, Hashimoto Y, Saigo K (1993) Chem Lett: 1117

    Google Scholar 

  49. Roe JM, Thomas EJ (1995) J Chem Soc Perkin 1: 359

    Google Scholar 

  50. Cossy J, Cases M, Pardo DG (1996) Tetrahedron Lett 37:8173

    CAS  Google Scholar 

  51. Corey EJ, Guzman-Perez A, Lazerwith SE (1997) J Am Chem Soc 119:11769

    CAS  Google Scholar 

  52. Honda T, Ono S, Mizutani H, Hallinan KO (1997) Tetrahedron Asymmetry 8:181

    CAS  Google Scholar 

  53. Shimizu M, Ishi K, Fujisawa T (1997) Chem Lett: 765

    Google Scholar 

  54. Wilkinson AL, Hanefeld U, Wilkinson B, Leadlay PF, Staunton J (1998) Tetrahedron Lett 39:9827

    CAS  Google Scholar 

  55. Miyazawa M, Oonuma S, Maruyama K, Miyashita M (1997) Chem Lett: 1191

    Google Scholar 

  56. Miyazawa M, Matsuoka E, Sasaki S, Oonuma S, Maruyama K, Miyashita M (1998) Chem Lett: 109

    Google Scholar 

  57. Hiscock SD, Hitchcock PB, Parsons PJ (1998) Tetrahedron 54:11567

    CAS  Google Scholar 

  58. Tanaka H, Kamikubo T, Yoshida N, Sakagami H, Taniguchi T, Ogasawara K (2001) Org Lett 3:679

    CAS  Google Scholar 

  59. Smitrovich JH, Boice GN, Qu C, DiMichele L, Nelson TD, Huffman MA, Murry J, McNamara J, Reider PJ (2002) Org Lett 4:1963

    CAS  Google Scholar 

  60. Stritzke K, Schulz S, Nishida R (2002) Eur J Org Chem: 3884

    Google Scholar 

  61. Zarbin PHG, Oliveira ARM, Simonelli F, Villar JAFP, Delay O Jr (2004) Tetrahedron Lett 45:7399

    CAS  Google Scholar 

  62. Fleming I, Terrett NK (1998) J Chem Soc Perkin 1: 2645

    Google Scholar 

  63. Uyehara T, Shida N, Yamamoto Y (1992) J Org Chem 57:3139

    CAS  Google Scholar 

  64. Jahn U, Hartmann P, Kaasalainen E (2004) Org Lett 6:257

    CAS  Google Scholar 

  65. Sibi MP, He L (2004) Org Lett 6:1749

    CAS  Google Scholar 

  66. Yadav JS, Reddy PMK, Reddy PV (2007) Tetrahedron Lett 48:1037

    CAS  Google Scholar 

  67. Blay G, Hernández-Olmos V, Pedro JR (2010) Org Lett 12:3058

    CAS  Google Scholar 

  68. Cid MB, Duce S, Morales S, Rodrigo E, García Ruano JL (2010) Org Lett 12:3586

    CAS  Google Scholar 

  69. Bindseil KU, Zeeck A (1993) Helv Chim Acta 76:150

    CAS  Google Scholar 

  70. Boddien C, Gorber-Nolte J, Zeeck A (1996) Liebigs Ann: 1381

    Google Scholar 

  71. Peed J, Domínguez IP, Davies IR, Cheeseman M, Taylor JE, Kociok-Köhn G, Bull SD (2011) Org Lett 13:3592

    CAS  Google Scholar 

  72. Renz M, Meunier B (1999) Eur J Org Chem: 737

    Google Scholar 

  73. Hacini S, Santelli M (1990) Tetrahedron 46:7787

    CAS  Google Scholar 

  74. Santelli-Rouvier C, Lefrère S, Santelli M (1994) Tetrahedron Lett 35:6101

    CAS  Google Scholar 

  75. Adger B, Teresa Bes M, Grogan G, McCague R, Pedragosa-Moreau S, Roberts SM, Villa R, Wan PWH, Willetts AJ (1995) J Chem Soc Chem Commun: 1563

    Google Scholar 

  76. Clissold C, Kelly CL, Lawrie KWM, Willis CL (1997) Tetrahedron Lett 38:8105

    CAS  Google Scholar 

  77. Yamamoto T, Ogura M, Amano A, Adachi K, Hagiwara T, Kanisawa T (2002) Tetrahedron Lett 43:9081

    CAS  Google Scholar 

  78. Chakraborty TK, Chandrasekaran S (1980) Tetrahedron Lett 21:1583

    CAS  Google Scholar 

  79. Rathore R, Vankar PS, Chandrasekaran S (1986) Tetrahedron Lett 27:4079

    CAS  Google Scholar 

  80. Schlecht MF, Kim H-J (1985) Tetrahedron Lett 26:127

    CAS  Google Scholar 

  81. Yamamoto M, Hirota M, Kishikawa K, Kohmoto S, Yamada K (1997) Synthesis: 937

    Google Scholar 

  82. Suzuki T, Morita K, Tsuchida M, Hiroi K (2002) Org Lett 4:2361

    CAS  Google Scholar 

  83. Schomaker JM, Travis BR, Borhan B (2003) Org Lett 5:3089

    CAS  Google Scholar 

  84. Yang C-G, Reich NW, Shi Z, He C (2005) Org Lett 7:4553

    CAS  Google Scholar 

  85. Mollat du Jourdin X, Noshi M, Fuchs PL (2009) Org Lett 11:543

    CAS  Google Scholar 

  86. Ramón DJ, Yus M (1990) Tetrahedron Lett 31:3767

    Google Scholar 

  87. Robin S, Huet F (1993) Tetrahedron Lett 34:2945

    CAS  Google Scholar 

  88. Oppolzer W, Walther E, Balado CP, De Brabander J (1997) Tetrahedron Lett 38:809

    CAS  Google Scholar 

  89. Kaku H, Tanaka M, Norimine Y, Miyashita Y, Suemune H, Sakai K (1997) Tetrahedron Asymmetry 8:195

    CAS  Google Scholar 

  90. Kishida M, Yamauchi N, Sawada K, Ohashi Y, Eguchi T, Kakinuma K (1997) J Chem Soc Perkin 1: 891

    Google Scholar 

  91. Shimizu M, Kamikubo T, Ogasawara K (1997) Tetrahedron Asymmetry 8:2519

    CAS  Google Scholar 

  92. Dujardin G, Rossignol S, Brown E (1998) Synthesis: 763

    Google Scholar 

  93. BouzBouz S, Popkin ME, Cossy J (2000) Org Lett 2:3449

    CAS  Google Scholar 

  94. Berry MB, Griffiths RJ, Sanganee MJ, Steel PG, Whelligan DK (2003) Tetrahedron Lett 44:9135

    CAS  Google Scholar 

  95. Casas J, Engqvist M, Ibrahem I, Kaynak B, Córdova A (2005) Angew Chem Int Ed 44:1343

    CAS  Google Scholar 

  96. Cardllina JH II, Moore RE, Arnold EV, Clardy J (1979) J Org Chem 44:4039

    Google Scholar 

  97. Torii S, Inokuchi T, Yoritaka K (1981) J Org Chem 46:5030

    CAS  Google Scholar 

  98. Greeves N, Lee W-M, Barkley JV (1997) Tetrahedron Lett 38:6453

    CAS  Google Scholar 

  99. Tan CK, Zhou L, Yeung Y-Y (2011) Org Lett 13:2738

    CAS  Google Scholar 

  100. Zhang W, Liu N, Schienebeck CM, Decloux K, Zheng S, Werness JB, Tang W (2012) Chem Eur J 18:7296

    CAS  Google Scholar 

  101. Pilli RA, Murta MM (1993) J Org Chem 58:338

    CAS  Google Scholar 

  102. Kobayashi K, Minakawa H, Sakurai H, Kujime S, Suginome H (1993) J Chem Soc Perkin 1: 3007

    Google Scholar 

  103. Bachi MD, Bosch E (1992) J Org Chem 57:4696

    CAS  Google Scholar 

  104. Ihara M, Setsu F, Shohda M, Taniguchi N, Fukumoto K (1994) Heterocycles 37:289

    CAS  Google Scholar 

  105. Chuang T-H, Fang J-M, Jiaang W-T, Tsai Y-M (1996) J Org Chem 61:1794

    CAS  Google Scholar 

  106. Hsu J-L, Chen C-T, Fang J-M (1999) Org Lett 1:1989

    CAS  Google Scholar 

  107. Annby U, Stenkula M (1993) Tetrahedron Lett 34:8545

    CAS  Google Scholar 

  108. Toyota M, Hirota M, Nishikawa Y, Fukumoto K, Ihara M (1998) J Org Chem 63:5895

    CAS  Google Scholar 

  109. Toyota M, Nishikawa Y, Fukumoto K (1998) Heterocycles 47:675

    CAS  Google Scholar 

  110. Tsunoi S, Ryu I, Sonoda N (1994) J Am Chem Soc 116:5473

    CAS  Google Scholar 

  111. Tsunoi S, Ryu I, Okuda T, Tanaka M, Komatsu M, Sonoda N (1998) J Am Chem Soc 120:8692

    CAS  Google Scholar 

  112. Kočovský P, Dunn V, Grech JM, Šrogl J, Mitchell WL (1996) Tetrahedron Lett 37:5585

    Google Scholar 

  113. Kramer JW, Joh DY, Coates GW (2007) Org Lett 9:5581

    CAS  Google Scholar 

  114. Sell MS, Xiong H, Rieke RD (1993) Tetrahedron Lett 34:6007

    CAS  Google Scholar 

  115. Rieke RD, Sell MS, Xiong H (1995) J Org Chem 60:5143

    CAS  Google Scholar 

  116. Kostas ID, Screttas CG (1997) J Org Chem 62:5575

    CAS  Google Scholar 

  117. Canonne P, Bélanger D, Lemay G, Foscolos GB (1981) J Org Chem 46:3091

    CAS  Google Scholar 

  118. Demir AS, Gross RS, Dunlap NK, Bashir-Hashemi A, Watt DS (1986) Tetrahedron Lett 27:5567

    CAS  Google Scholar 

  119. Brandänge S, Leijonmarck H (1992) Tetrahedron Lett 33:3025

    Google Scholar 

  120. Marson CM, Randall L, Winter MJ (1994) Tetrahedron Lett 35:6717

    CAS  Google Scholar 

  121. Imamoto T, Hatajima T, Yoshizawa T (1994) Tetrahedron Lett 35:7805

    CAS  Google Scholar 

  122. Kumar A, Dittmer DC (1994) J Org Chem 59:4760

    CAS  Google Scholar 

  123. Satoh T, Kurihara T (1998) Tetrahedron Lett 39:9215

    CAS  Google Scholar 

  124. Francisco CG, Martin CG, Suárez E (1998) J Org Chem 63:2099

    CAS  Google Scholar 

  125. Mongin C, Gruet K, Lugan N, Mathieu R (2000) Tetrahedron Lett 41:7341

    CAS  Google Scholar 

  126. Ogibin YN, Terent’ev AO, Kutkin AV, Nikishin GI (2002) Tetrahedron Lett 43:1321

    CAS  Google Scholar 

  127. Wang L, Thai K, Gravel M (2009) Org Lett 11:891

    CAS  Google Scholar 

Download references

Acknowledgments

K.P.K. thanks DST, New Delhi, for the award of the Swarnajayanti fellowship, and K.P. thanks CSIR, New Delhi, for a fellowship. Further, we thank Sankar R. Suravarapu for his valuable initial work on this program.

Author information

Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, Maharashtra, India

    Kalanidhi Palanichamy & Krishna P. Kaliappan

Authors
  1. Kalanidhi Palanichamy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Krishna P. Kaliappan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Krishna P. Kaliappan .

Editor information

Editors and Affiliations

  1. ESPCI, Laboratory of Organic Chemistry, Paris Cedex 05, France

    Janine Cossy

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Palanichamy, K., Kaliappan, K.P. (2014). Synthesis of Saturated Six-Membered Ring Lactones. In: Cossy, J. (eds) Synthesis of Saturated Oxygenated Heterocycles I. Topics in Heterocyclic Chemistry, vol 35. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-41473-2_3

Download citation

Publish with us

Policies and ethics

Search

Navigation