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Total syntheses of epothilones B and D: applications of allylstannanes in organic synthesis

✍ Scribed by Nathaniel Martin; Eric J Thomas

Book ID
104231843
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
83 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Following exploratory studies which culminated in syntheses of the alcohol 16, a total synthesis of epothilones B and D is reported in which the trisubstituted 12,13-double-bond is introduced stereoselectively using the tin(IV) bromide-promoted reaction between the allylstannane 22 and the aldehyde 17. A Barton deoxygenation then gave the C( 7) C(15) fragment 25. After development of the thiazole containing side-chain, an aldol condensation with the ethyl ketone 36 gave the adduct 37 which was taken through to epothilone D 2 and then to epothilone B 1.

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