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

Tadross, Pamela M. and Virgil, Scott C. and Stoltz, Brian M. (2010) Aryne Acyl-Alkylation in the General and Convergent Synthesis of Benzannulated Macrolactone Natural Products: An Enantioselective Synthesis of (−)-Curvularin. Organic Letters, 12 (7). pp. 1612-1614. ISSN 1523-7060. http://resolver.caltech.edu/CaltechAUTHORS:20100413-105259618

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol100335y DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol100335yPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
Gordon and Betty Moore Foundation UNSPECIFIED
Abbott UNSPECIFIED
Amgen UNSPECIFIED
Boehringer-Ingelheim UNSPECIFIED
Bristol-Myers Squibb UNSPECIFIED
Merck UNSPECIFIED
Sigma-Aldrich UNSPECIFIED
California HIV/AIDS Research Program UNSPECIFIED
CaltechUNSPECIFIED
Record Number:CaltechAUTHORS:20100413-105259618
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20100413-105259618
Official Citation:Aryne Acyl-Alkylation in the General and Convergent Synthesis of Benzannulated Macrolactone Natural Products: An Enantioselective Synthesis of (−)-Curvularin Pamela M. Tadross, Scott C. Virgil, Brian M. Stoltz Organic Letters 2010 12 (7), 1612-1614
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:17954
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:28 Apr 2010 18:35
Last Modified:15 Feb 2017 19:36

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