Synthesis of β,γ-disubstituted-γ-lactones through a Johnson-Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

Tetrahedron Asymmetry

Volumn 20, Issue 24, 2009, Pages 2835-2844

  Fernandes, Rodney A ^a   Ingle, Arun B ^a   Chavan, Vijay P ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CANADENSOLIDE; GAMMA LACTONE DERIVATIVE; LACTONE; NATURAL PRODUCT; SANTILINOLIDE; SPOROTHRIOLIDE; UNCLASSIFIED DRUG; XYLOBOVIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 74049121614     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.11.018     Document Type: Article

References (52)

1. Abate D., Abraham W.-R., and Meyer H. Phytochemistry 44 (1997) 1443
2. McCorkindale N.J., Wright J.L.C., Brian P.W., Clarke S.M., and Hutchinson S.A. Tetrahedron Lett. 6 (1968) 727
3. Krohn K., Ludewig K., Aust H.J., Draeger S., and Schulz B. J. Antibiot. 47 (1994) 113
4. Epstein W.W., and Gaudioso L.A. J. Org. Chem. 44 (1979) 3113
5. Kato M., Tanaka R., and Yoshikoshi A. J. Chem. Soc., Chem. Commun. (1971) 1561
6. Kato M., Kageyama M., Tanaka R., Kuwahara K., and Yoshikoshi A. J. Org. Chem. 40 (1975) 1932
7. Carlson R.M., and Oyler A.R. J. Org. Chem. 41 (1976) 4065
8. Kosugi H., Sekiguchi S., Sekita R., and Uda H. Bull. Chem. Soc. Jpn. 49 (1976) 520
9. Anderson R.C., and Fraser-Reid B. Tetrahedron Lett. 19 (1978) 3233
10. Ohrui H., Sueda N., and Kuzuhara H. Nippon Kagaku Kaishi (1981) 769
11. Tsuboi S., Fujita H., Muranaka K., Seko K., and Takeda A. Chem. Lett. (1982) 1909
12. Sakai T., Yoshida M., Kohmoto S., Utaka M., and Takeda A. Tetrahedron Lett. 23 (1982) 5185
13. Anderson R.C., and Fraser-Reid B. J. Org. Chem. 50 (1985) 4786
14. Tsuboi S., Muranaka K., Sakai T., and Takeda A. J. Org. Chem. 51 (1986) 4944
15. Tochtermann W., Schroeder G.R., Snatzke G., Peters E.M., Peters K., and Von Schnering H.G. Chem. Ber. 121 (1988) 1625
16. Honda T., Kobayashi Y., and Tsubuki M. Tetrahedron Lett. 31 (1990) 4891
17. Sharma G.V.M., and Vepachedu S.R. Tetrahedron 47 (1991) 519
18. Honda T., Kobayashi Y., and Tsubuki M. Tetrahedron 49 (1993) 1211
19. Nubbemeyer U. Synthesis (1993) 1120
20. Sharma G.V.M., and Krishnudu K. Tetrahedron Lett. 36 (1995) 2661
21. Al-Abed Y., Naz N., Mootoo D., and Voelter W. Tetrahedron Lett. 37 (1996) 8641
22. Yu M., Lynch V., and Pagenkopf B.L. Org. Lett. 3 (2001) 2563
23. Mondal S., and Ghosh S. Tetrahedron 64 (2008) 2359
24. Fernandes R.A. Eur. J. Org. Chem. (2007) 5064
25. Fernandes R.A. Tetrahedron: Asymmetry 19 (2008) 15
26. Fernandes R.A., and Chavan V.P. Tetrahedron Lett. 49 (2008) 3899
27. Fernandes R.A., Chavan V.P., and Ingle A.B. Tetrahedron Lett. 49 (2008) 6341
28. Fernandes R.A., Dhall A., and Ingle A.B. Tetrahedron Lett. 50 (2009) 5903
29. Fernandes R.A., and Chowdhury A.K. J. Org. Chem 74 (2009) 8826
30. Fernandes R.A., and Ingel A.B. Syn. lett (2010) 158
31. Fernandes R.A., and Ingle A.B. Tetrahedron Lett. 50 (2009) 1122
32. Reviews:. Johnson R.A., and Sharpless K.B. In: Ojima I. (Ed). Asymmetric Catalysis in Organic Synthesis (1993), VCH, New York 227
33. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483
34. Bolm C., Hildebrand J.P., and Muniz K. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York 399
35. Martin D.C., Hoult D.A., and Andrew D.A. Aust. J. Chem. 54 (2001) 391
36. Enantiomeric excess was determined by chiral HPLC. Column: Chiralpak IA No. IA00CE-KL063, eluent: n-hexane/i-PrOH (95:5), flow rate: 0.5 mL/min, UV detector: 240 nm.
37. Boruwa J., and Barua N.C. Tetrahedron 62 (2006) 1193
38. Wan S., Green M.E., Park J.-H., and Floreancig P.E. Org. Lett. 9 (2007) 5385
39. For the Johnson-Claisen rearrangement see:. Johnson W.S., Werthemann L., Bartlett W.R., Brocksom T.J., Li T.-T., Faulkner D.J., and Peterson M.R. J. Am. Chem. Soc. 92 (1970) 741
40. Hiyama T., Kobayashi K., and Fujita M. Tetrahedron Lett. 25 (1984) 4959
41. Ziegler F. Chem. Rev. 88 (1988) 1423
42. Agami C., Couty F., and Evano G. Tetrahedron Lett. 41 (2000) 8301
43. Brenna E., Fuganti C., Gatti F.G., Passoni M., and Serra S. Tetrahedron: Asymmetry 14 (2003) 2401
44. Chan K.-K., Cohen N., De Noble J.P., Specian Jr. A.C., and Saucy G. J. Org. Chem. 41 (1976) 3497
45. 1H NMR of the mixture. Here anti/syn refers to the C3/C4 relative configuration of protons. (b) The reaction was not continued over 4 h so as to avoid the formation of higher amounts of the anti-diastereomer. When the reaction was carried out over shorter periods, lower yields were obtained with no change in the anti/syn ratio.
46. The relative configuration of 20a and 20b is based on the comparison of the chemical shifts of Hb protons in the lactones. In 20a, the Hb proton is syn to the vinyl group and is shielded to δ 4.12 as compared to Hb (δ 4.38) in 20b.{A figure is presented}
47. The syn-geometry in 20b is further confirmed after the ozonolysis reaction by the fact that it cyclizes to give the γ-(lactone-lactol) intermediate 6b (Scheme 3).
48. 5i,5s
49. 3CN, NaH/THF and NaHMDS/THF were attempted to epimerize the -carbon centre of aldehyde 24, but they failed to produce 6c.
50. Valverde S., Herradon B., Rabanal R.M., and Martin-Lomas M. Can. J. Chem. 65 (1987) 332
51. (a) Gao, D.; O'Doherty, G. A. Org. Lett. 2005, 7, 1069. (b) Gao, D.; O'Doherty, G. A. J. Org. Chem. 2005, 70, 9932. (c) The enantiomeric excess reported in the synthesis of 26 is only 85% ee. Hence the compound 26 prepared from (R,R)-diethyl tartrate was used further.
52. 5o