Issue 10, 2011
From the journal:

Organic & Biomolecular Chemistry

Total synthesis and absolute configuration of malyngamide W†

Xian-Liang Qi,a   Jun-Tao Zhang,a   Jian-Peng Fenga  and  Xiao-Ping Cao*a  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China
E-mail: caoxplzu@163.com
Fax: 86 931 8912582

Abstract

A concise enantioselective synthesis of malyngamide W (1) and its 2′-epimer was described. The strategy was based on three key steps: (1) ozonolysis of compound 11 which was derived from (R)-(−)-carvone 8, followed by copper-iron-catalyzed rearrangement to give the key cyclohex-2-enone intermediate 5, (2) Nozaki–Hiyama–Kishi coupling reaction between aldehyde 4 and iodide 14 to afford alcohol 3, and (3) asymmetric (R)-CBS reduction of the ketone functionality in compound 21 to establish the C-2′ chiral center in the target compound 1. The absolute configuration of malyngamide W (1) was thus confirmed via the synthesis of 1 and 2′-epi-1.

Graphical abstract: Total synthesis and absolute configuration of malyngamide W

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Article information

DOI
https://doi.org/10.1039/C0OB01118E
Article type
Paper
Submitted
06 Dec 2010
Accepted
25 Feb 2011
First published
25 Feb 2011

Org. Biomol. Chem., 2011,9, 3817-3824

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Total synthesis and absolute configuration of malyngamide W

X. Qi, J. Zhang, J. Feng and X. Cao, Org. Biomol. Chem., 2011, 9, 3817 DOI: 10.1039/C0OB01118E

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