Unified Synthesis of C19-C26 Subunits of Amphidinolides B1, B2, and B3 by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2004 Mar 31

PMID 15049660

Citations 12

Authors

Wei Zhang

Rich G Carter

Alexandre F T Yokochi

Affiliations

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Abstract

The efficient synthesis of the C(19)-C(26) subunit of amphidinolide B(1) and B(2) has been completed using a boron-mediated aldol reaction. The synthesis of the C(19)-C(26) subunit of amphidinolide B(3) has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

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