An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A.

Tetrahedron letters ·Vol. 44 ·No. 20 ·2003-05-12 ·Pages 3967-3969

Ghosh AK, Kim JH

Abstract

A stereocontrolled synthesis of the C1-C9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral β-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an α,β-unsaturated δ-lactone.

Authors & Affiliations

2 authors, click to expand affiliations / ORCID

Ghosh Arun K

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA.

Kim Jae-Hun

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607, USA.

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Article Info

Journal

Tetrahedron letters

Abbr.

Tetrahedron Lett

ISSN

0040-4039

DOI

10.1016/S0040-4039(03)00744-5

Published

2003-05-12

Epub

2003-00-24

Pages

3967-3969

Language

English

Region

England

NLM ID

2984819R

PMCID

PMC6214207

Grants

NIGMS NIH HHS · R01 GM053386 · United States

External Links

PubMed source DOI: 10.1016/S0040-4039(03)00744-5 PMC Full Text View journal details

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An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A.

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