CaltechAUTHORS
Published April 2, 2010 | Version Supplemental Material
Journal Article Open

Aryne Acyl-Alkylation in the General and Convergent Synthesis of Benzannulated Macrolactone Natural Products: An Enantioselective Synthesis of (−)-Curvularin

Creators

  • 1. ROR icon California Institute of Technology

Abstract

A general approach for the synthesis of benzannulated macrolactone natural products utilizing an aryne acyl-alkylation reaction is described. Toward this end, the total syntheses of the natural products (−)-curvularin, curvulin, and (−)-diplodialide C are reported. Furthermore, the aryne insertion technology has enabled the rapid conversion of simple diplodialide natural products to curvularin, thereby connecting these two biosynthetically distinct classes of compounds via synthetic methods.

Additional Information

© 2010 American Chemical Society. Published In Issue April 02, 2010; Article ASAP March 02, 2010; Received: February 9, 2010. Publication Date (Web): March 2, 2010. We thank The Gordon and Betty Moore Foundation, Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, Sigma-Aldrich, The California HIV/AIDS Research Program (fellowship to P.M.T.), and Caltech for generous funding.

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Supplemental Material - ol100335y_si_001.pdf

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Additional details

Identifiers

Eprint ID
17954
Resolver ID
CaltechAUTHORS:20100413-105259618

Funding

Gordon and Betty Moore Foundation
Abbott
Amgen
Boehringer-Ingelheim
Bristol-Myers Squibb
Merck
Sigma-Aldrich
California HIV/AIDS Research Program
Caltech

Dates

Created
2010-04-28
Created from EPrint's datestamp field
Updated
2021-11-08
Created from EPrint's last_modified field