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First total synthesis of (+)-Vedelianin, a potent antiproliferative agent.

ABSTRACT: The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S, 3R, 4aR, 9aR)-isomer.

SUBMITTER: Topczewski JJ

PROVIDER: S-EPMC3204860 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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First total synthesis of (+)-Vedelianin, a potent antiproliferative agent.

Topczewski Joseph J JJ Wiemer David F DF

Tetrahedron letters 20110401 14

The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S, 3R, 4aR, 9aR)-isomer. ...[more]

PMID: 22053119

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