Concise and stereocontrolled assembly of substituted dihydropyrans. Synthetic studies towards the trans the dioxadecalin subunit of okadaic acid

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2899-2902

  Markó, István E ^a   Dobbs, Adrian P ^a   Scheirmann, Vincent ^a   Chellé, François ^a   Bayston, Daniel J ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

DECALIN DERIVATIVE; OKADAIC ACID; PYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030914643     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00471-1     Document Type: Article

References (20)

1. (a) Cyert, M.S.; Thorner, J. Cell, 1989, 57, 891;
2. (b) Nishiwaki, S.; Fujiki, H.; Saganuma, M.; Furuya-Suguri, H.; Matsushima, R.; Iida, Y.; Ojika, M; Yamada, K.; Uemura, D.; Yasumoto, T.; Schmitz, F.J.; Sugimura, T. Carcinogenesis, 1990, 11, 1837;
3. (c) Cohen, P.; Holmes, C.F.B.; Tsukitani, Y. Trends Biochem. Sci., 1990, 15, 98. See also: Brugge, J.S. Chem. Biol., 1994, introductory issue.
4. (c) Cohen, P.; Holmes, C.F.B.; Tsukitani, Y. Trends Biochem. Sci., 1990, 15, 98. See also: Brugge, J.S. Chem. Biol., 1994, introductory issue.
5. Isobe, M.; Ichikawa, Y.; Bai, D.-L.; Masaki, H.; Goto, T. Tetrahedron, 1987, 43, 4767 and references cited therein.
6. Markó, I.E.; Chellé, F. Tetrahedron Lett., preceding communication.
7. See for example: (a) Blumenkopf, T.A.; Look, G.G.; Overman, L.E. J. Am. Chem. Soc., 1990, 112, 4399 and references cited therein;
8. (b) Hoffmann, R.W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629;
9. (c) Burke, S.D.; Kort, M.E.; Strickland, S.M.S.; Organ, H.M.; Silks, L.A. Tetrahedron Lett., 1994, 55, 1503.
10. For reviews, see: (a) Schinzer, D.; Langkopf, E. Chem. Rev., 1995, 95, 1375;
11. (b) Colvin, E.W. Silicon Reagents in Organic Synthesis, Acad. Press, 1988, London.
12. Markó, I.E., Bayston, D.J. Synthesis, 1996, 297 and references cited therein.
13. This observation suggests that oxy-Cope rearrangement does not take place under these conditions.
14. Opening of this simple epoxide by trimethylsilyl alkynyl lithium under a variety of conditions failed to give 19. Only the method of Yamaguchi afforded the desired homopropargylic alcohol 19, albeit in a modest 30% yield. Yamaguchi, M.; Nobayashi, Y.; Hirao, I. Tetrahedron, 1984, 40, 4261.
15. (a) Matthews, R.S., Eickhoff, D.J. J. Org. Chem., 1985, 50, 3923;
16. (b) Nicolaou, K.C.; Webber, S.E.; Ramphal, J.; Abe, Y. Angew. Chem. Int. Ed. Engl., 1987, 26, 1019.
17. On, H.P.; Lewis, W.; Zweifel, G. Synthesis, 1981, 999.
18. Compound 23 was prepared by esterification of the primary alcohol function of 21 followed by catalytic dihydroxylation (Van Rheenen, V.; Kelly, R.C.; Cha, D.F. Tetrahedron Lett., 1973, 1976) and exhaustive acetylation.
19. 26 susbtituent.
20. Nicolaou, K.C.; Prasad, C.V.C.; Somers, P.K.; Hwang, C.-K. J. Am. Chem. Soc., 1989, 111, 5330.