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Improved total synthesis of the potent HDAC inhibitor FK228 (FR-901228).


ABSTRACT: A scaleable synthesis of the potent histone deacetylase (HDAC) inhibitor FK228 is described. A reliable strategy for preparing the key beta-hydroxy mercapto heptenoic acid partner was accomplished in nine steps and 13% overall yield. A Noyori asymmetric hydrogen-transfer reaction established the hydroxyl stereochemistry in >99:1 er via the reduction of a propargylic ketone.

SUBMITTER: Greshock TJ 

PROVIDER: S-EPMC3097137 | biostudies-literature | 2008 Feb

REPOSITORIES: biostudies-literature

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Improved total synthesis of the potent HDAC inhibitor FK228 (FR-901228).

Greshock Thomas J TJ   Johns Deidre M DM   Noguchi Yasuo Y   Williams Robert M RM  

Organic letters 20080119 4


A scaleable synthesis of the potent histone deacetylase (HDAC) inhibitor FK228 is described. A reliable strategy for preparing the key beta-hydroxy mercapto heptenoic acid partner was accomplished in nine steps and 13% overall yield. A Noyori asymmetric hydrogen-transfer reaction established the hydroxyl stereochemistry in >99:1 er via the reduction of a propargylic ketone. ...[more]

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