A Chemoenzymatic Synthesis of the C1-C9 Fragment of Bryostatin. Unusual Diastereoselectivity During a Mukaiyama Aldol Condensation
- 1 January 1990
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1990 (08) , 448-450
- https://doi.org/10.1055/s-1990-21122
Abstract
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.Keywords
This publication has 0 references indexed in Scilit: