12 Conclusions
In view of the biological importance of the δ-lactone moiety, extensive efforts have
been devoted for the development of various methods for the synthesis of saturated
δ-lactones. Among the various methods, the more classical methods include
lactonization of the δ-hydroxy acid derivatives, Baeyer–Villiger oxidation of
cyclopentanones, and oxidation of lactols. Besides, more challenging and attractive
methods such as oxidative lactonization, radical cyclization, and carbonylation
have also been used efficiently for the synthesis of δ-lactones. The past two decades
have witnessed remarkable growth in the development of catalytic and asymmetric
methods for the synthesis of δ-lactones in optically pure form. In the next decade,
new and more exciting advances in the development of efficient and catalytic
enantioselective methods and their application in the synthesis of complex
δ-lactone natural products can be expected.
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.
References
1. Rasmussen JK (1977) Synthesis: 91
2. Reetz MT (1982) Angew Chem Int Ed 21:96
3. Rocca JR, Tumlinson JH, Glancey BM, Lofren CS (1983) Tetrahedron Lett 24:1889
4. Gunasekara SP, Longley RE, Schulte GK (1991) J Org Chem 56:1346
5. Endo A, Kuroda M, Tsujita M (1976) J Antibiot 29:1346
6. Barua NC, Schmidt RR (1986) Synthesis: 1067
7. Thompson CM (1987) Tetrahedron Lett 28:4243
8. Mori K (1989) Tetrahedron 45:3233
9. Boucard V, Broustal G, Campagne JM (2007) Eur J Org Chem: 225
10. Florence GJ, Gardner NM, Paterson I (2008) Nat Prod Rep 25:342
11. Chiu P, Leung LT, Ko CBB (2010) Nat Prod Rep 27:1066
12. Schreiber SL (1991) Science 251:283
13. Rosen MK, Schreiber SL (1992) Angew Chem Int Ed 31:384
14. Endo A (1979) J Antibiot 32:854
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-Scho ¨nberg G, Hensens O,
Hirschfield J, Hoogsteen K, Liesch J (1980) Proc Natl Acad Sci USA 77:3957
16. Endo A, Kuroda M, Tsujita Y (1976) J Antibiot 26:1346
17. Brown AG, Smale TC, King TJ, Hasenkamp R, Thompson RH (1976) J Chem Soc Perkin 1:
1165
18. Anliker R, Dvornik D, Gubler K, Heusser H, Prelog V (1956) Helv Chim Acta 39:1785
19. Djerassi C, Zderic JA (1956) J Am Chem Soc 78:6390
20. Li ZL, Pan DJ, Hu CQ, Wu QL, Yang SS, Xu GY (1982) Acta Chimi Sin 40:447
21. Li ZL, Pan DJ, Wu QL, Xu GY (1982) Acta Chimi Sin 40:757
22. Zhou BN, Ying B, Song GQ, Chen ZX, Han J, Yan YF (1983) Planta Med 47:35
23. Hamburger M, Shieh H, Pezzuto J, Cordell GA, Zhou BN (1988) Planta Med 54:579
Synthesis of Saturated Six-Membered Ring Lactones
137
In view of the biological importance of the δ-lactone moiety, extensive efforts have
been devoted for the development of various methods for the synthesis of saturated
δ-lactones. Among the various methods, the more classical methods include
lactonization of the δ-hydroxy acid derivatives, Baeyer–Villiger oxidation of
cyclopentanones, and oxidation of lactols. Besides, more challenging and attractive
methods such as oxidative lactonization, radical cyclization, and carbonylation
have also been used efficiently for the synthesis of δ-lactones. The past two decades
have witnessed remarkable growth in the development of catalytic and asymmetric
methods for the synthesis of δ-lactones in optically pure form. In the next decade,
new and more exciting advances in the development of efficient and catalytic
enantioselective methods and their application in the synthesis of complex
δ-lactone natural products can be expected.
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.
References
1. Rasmussen JK (1977) Synthesis: 91
2. Reetz MT (1982) Angew Chem Int Ed 21:96
3. Rocca JR, Tumlinson JH, Glancey BM, Lofren CS (1983) Tetrahedron Lett 24:1889
4. Gunasekara SP, Longley RE, Schulte GK (1991) J Org Chem 56:1346
5. Endo A, Kuroda M, Tsujita M (1976) J Antibiot 29:1346
6. Barua NC, Schmidt RR (1986) Synthesis: 1067
7. Thompson CM (1987) Tetrahedron Lett 28:4243
8. Mori K (1989) Tetrahedron 45:3233
9. Boucard V, Broustal G, Campagne JM (2007) Eur J Org Chem: 225
10. Florence GJ, Gardner NM, Paterson I (2008) Nat Prod Rep 25:342
11. Chiu P, Leung LT, Ko CBB (2010) Nat Prod Rep 27:1066
12. Schreiber SL (1991) Science 251:283
13. Rosen MK, Schreiber SL (1992) Angew Chem Int Ed 31:384
14. Endo A (1979) J Antibiot 32:854
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-Scho ¨nberg G, Hensens O,
Hirschfield J, Hoogsteen K, Liesch J (1980) Proc Natl Acad Sci USA 77:3957
16. Endo A, Kuroda M, Tsujita Y (1976) J Antibiot 26:1346
17. Brown AG, Smale TC, King TJ, Hasenkamp R, Thompson RH (1976) J Chem Soc Perkin 1:
1165
18. Anliker R, Dvornik D, Gubler K, Heusser H, Prelog V (1956) Helv Chim Acta 39:1785
19. Djerassi C, Zderic JA (1956) J Am Chem Soc 78:6390
20. Li ZL, Pan DJ, Hu CQ, Wu QL, Yang SS, Xu GY (1982) Acta Chimi Sin 40:447
21. Li ZL, Pan DJ, Wu QL, Xu GY (1982) Acta Chimi Sin 40:757
22. Zhou BN, Ying B, Song GQ, Chen ZX, Han J, Yan YF (1983) Planta Med 47:35
23. Hamburger M, Shieh H, Pezzuto J, Cordell GA, Zhou BN (1988) Planta Med 54:579
Synthesis of Saturated Six-Membered Ring Lactones
137