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A concise, total synthesis of the TMC-95A/B proteasome inhibitors.

ABSTRACT: A concise, total synthesis of the proteasome inhibitors TMC-95A/B has been accomplished. The synthesis features the use of an L-serine-derived E-selective modified Julia olefination reaction to ultimately control the stereochemical outcome of the highly oxidized tryptophan fragment. Additionally, the limited use of protecting groups at a late stage of the total synthesis allowed for its completion in an efficient manner.

SUBMITTER: Albrecht BK

PROVIDER: S-EPMC514414 | biostudies-literature | 2004 Aug

REPOSITORIES: biostudies-literature

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A concise, total synthesis of the TMC-95A/B proteasome inhibitors.

Albrecht Brian K BK Williams Robert M RM

Proceedings of the National Academy of Sciences of the United States of America 20040526 33

A concise, total synthesis of the proteasome inhibitors TMC-95A/B has been accomplished. The synthesis features the use of an L-serine-derived E-selective modified Julia olefination reaction to ultimately control the stereochemical outcome of the highly oxidized tryptophan fragment. Additionally, the limited use of protecting groups at a late stage of the total synthesis allowed for its completion in an efficient manner. ...[more]

PMID: 15163792

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