A Chemoenzymatic Synthesis of the C1-C9 Fragment of Bryostatin. Unusual Diastereoselectivity During a Mukaiyama Aldol Condensation

René Roy; Allan W. Rey

doi:10.1055/s-1990-21122

Synlett 1990; 1990(8): 448-450
DOI: 10.1055/s-1990-21122

letter

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A Chemoenzymatic Synthesis of the C1-C9 Fragment of Bryostatin. Unusual Diastereoselectivity During a Mukaiyama Aldol Condensation

René Roy^* , Allan W. Rey

^*Department of Chemistry, University of Ottawa, Ottawa, Ontario Canada K1N 6N5

Abstract

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A practical route to the C1-C9 segment of (+)-Bryostatin 1 (1) in forms suitable for both synthetic elaboration and biological studies has been achieved via a single disconnection. The key step involved a diastereoselective Mukaiyama aldol condensation of diketene derived subunit S-tert-butyl 2,2-dimethyl-3-(trimethylsiloxy)-3-butenethioate (5) and chiral methoxymethyl-protected methyl (3R)-3-hydroxy-5-oxopentanoate 4 obtained by an enzyme catalyzed enantioselective hydrolysis of a prochiral diester using immobilized α-chymotrypsin.

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