Fluorous Mixture Synthesis of (-)-dictyostatin and Three Stereoisomers

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2006 Jan 18

PMID 16408900

Citations 14

Authors

Yoshikazu Fukui

Arndt M Bruckner

Youseung Shin

Raghavan Balachandran

Billy W Day

Dennis P Curran

Affiliations

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Abstract

[reaction: see text] A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostatin and three C6,C7 stereoisomers. Biological evaluation showed that the monoepimers of the natural product retained highly potent activity.

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