Synthesis of the spiroketal fragment of bistramide A via an exocyclic enol ether

Tetrahedron Letters

Volumn 51, Issue 35, 2010, Pages 4599-4601

  Tomas, Loïc ^a   Gueyrard, David ^a   Goekjian, Peter G ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Bisatratene; Bistramide; Enol ethers; Julia Kocienski reagents; Lactone; Natural product synthesis; Spiroketal

Indexed keywords

ACETAL DERIVATIVE; BISTRAMIDE A; ETHER DERIVATIVE; LACTONE; SPIRO COMPOUND; SULFONE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CYCLIZATION; HORNER EMMONS OLEFINATION; JULIA KOCIENSKI OLEFINATION; OLEFINATION; REACTION ANALYSIS; SYNTHESIS;

EID: 77955659805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.006     Document Type: Article

References (21)

1. D. Gouiffès, S. Moreau, N. Helbecque, J.L. Bernier, J.P. Hénichart, Y. Barbin, D. Laurent, and J.F. Verbist Tetrahedron 44 1988 451 459
2. J.F. Biard, C. Roussakis, J.M. Kornprobst, D. Gouiffes-Barbin, J.F. Verbist, P. Cotelle, M.P. Foster, C.M. Ireland, and C. Debitus J. Nat. Prod. 7 1994 1336 1345
3. A.V. Statsuk, D. Liu, and S.A. Kozmin J. Am. Chem. Soc. 126 2004 9546 9547
4. M.T. Crimmins, and A.C. DeBaillie J. Am. Chem. Soc. 128 2006 4936 4937
5. J.T. Lowe, I.E. Wrona, and J.S. Panek Org. Lett. 9 2007 327 330
6. J.S. Yadav, and L. Chetia Org. Lett. 9 2007 4587 4589
7. P. Wipf, Y. Uto, and S. Yoshimura Chem. Eur. J. 8 2002 1670 1681
8. P. Wipf, and T.D. Hopkins Chem. Commun. 27 2005 3421 3423
9. B. Bourdon, M. Corbet, P. Fontaine, P.G. Goekjian, and D. Gueyrard Tetrahedron Lett. 49 2008 750 754
10. S.B. Moilanen, J.S. Potuzak, and D.S. Tan J. Am. Chem. Soc. 128 2006 1792 1793
11. M. Corbet, B. Bourdon, D. Gueyrard, and P.G. Goekjian Tetrahedron Lett. 49 2008 747 749
12. A. Sharma, P. Iyer, S. Gamre, and S. Chattopadhyay Synthesis 2004 1037 1040
13. S. Hanessian, and K. Sumi Synthesis 1991 1083 1089
14. P.R. Blakemore, D.K.H. Ho, and W. Mieke Nap Org. Biomol. Chem. 3 2005 1365 1368
15. D. Gueyrard, R. Haddoub, A. Salem, N. Said Bacar, and P.G. Goekjian Synlett 2005 520 522
16. A more detailed report of the Lewis acid-catalyzed enol ether synthesis will appear in due course.
17. + 491.2594, found 491.2593.
18. J.B. Baudin, G. Hareau, S.A. Julia, and O. Ruel Tetrahedron Lett. 32 1991 1175 1178
19. J.B. Baudin, G. Hareau, S.A. Julia, R. Lorne, and O. Ruel Bull. Soc. Chim. Fr. 130 1993 856 878
20. P.R. Blakemore J. Chem. Soc. Perkin Trans. 1 23 2002 2563 2585
21. The working hypothesis behind this procedure is that the fragmentation is expected to have a positive entropy of activation and thus a strictly enthalpic barrier; higher temperatures will therefore favor the fragmentation over possible side reactions. For a discussion, please see for example: F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry, Part A 1977 Plenum New York Chapter 4, p 139