Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions

Wei Zhang; Rich G Carter; Alexandre F T Yokochi

doi:10.1021/jo035829l

Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions

J Org Chem. 2004 Apr 2;69(7):2569-72. doi: 10.1021/jo035829l.

Authors

Wei Zhang¹, Rich G Carter, Alexandre F T Yokochi

Affiliation

¹ Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331, USA.

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Catalysis
Indicators and Reagents
Macrolides / chemical synthesis*
Models, Molecular
Molecular Structure

Substances

Bridged Bicyclo Compounds, Heterocyclic
Indicators and Reagents
Macrolides
amphidinolide D

Abstract

Publication types

MeSH terms

Substances

Grants and funding