Progress towards an intramolecular Diels-Alder ring-expansion approach to taxinine: The interplay of Lewis acids and high pressure

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2723-2727

  Phillips, Andrew J ^a   Morris, Jonathan C ^a   Abell, Andrew D ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; TAXININE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; PRESSURE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034620923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00248-3     Document Type: Article

References (20)

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2. Hosoyama, H.; Shigemori, H.; Tomida, A.; Tsuro, T.; Kobayashi, J. Bioorg. Med. Chem. Lett. 1999, 9, 389.
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7. (b) Rigby, J. H.; Senanayake, C. J. Org. Chem. 1987, 52, 4634.
8. 2Si: 322.23281; found: 322.23323.
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10. Bromodiene 2 is readily prepared in large quantities from 2,3-dimethylbut-2-ene as described by Magnus, P.; Westwood, N.; Spyvee, M.; Frost, C.; Linnane, P.; Tavares, F.; Lynch, V. Tetrahedron 1999, 55, 6435 and references cited therein.
11. Shea, K. J.; Gilman, J. W. Tetrahedron Lett. 1983, 24, 657.
12. Rigorous purification of the boron trifluoride diethyl etherate, and all efforts to ensure complete exclusion of moisture failed to suppress desilylation.
13. The numbering system used is based on the system used for taxanes.
14. -3.
15. It is conceivable that the cyclization could occur via either a chair or a twist chair conformation for the forming seven-membered ring. We favor the chair conformation because modeling indicated the twist-chair conformation has a potential unfavorable interaction between the silyl ether and the diene methyl group:
16. For a review of high pressure in synthesis, see: Matsumoto, K.; Sera, A.; Uchida, T. Synthesis 1985, 1.
17. For a study of a type I IMDA reaction and discussion of the effect of pressure on competing processes, see: Diedrich, M. K.; Klarner, F. G. J. Am. Chem. Soc. 1998, 120, 6212.
18. Analysis was carried out on the crude product without purification.
19. Recent examples of Diels-Alder reactions under pressure include: (a) Brickwood, A. C.; Drew, M. G. B.; Harwood, L. M.; Ishikawa, T.; Marais, P.; Morisson, V. J. Chem. Soc., Perkin Trans. 1 1999, 913.
20. (b) Araki, Y.; Konoike, T. J. Org. Chem. 1997, 62, 529.