Issue 22, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthetic studies on the mycolactone core†

Kwang-Seuk Ko,‡a   Matthew D. Alexander,‡ab   Shaun D. Fontaine,a   James E. Biggs-Houck,a   James J. La Claira  and  Michael D. Burkart*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA, USA
E-mail: mburkart@ucsd.edu
Fax: +1-858-822-2182

b Current Address: TetraLogic Pharmaceuticals, 343 Phoenixville Pike, Malvern, PA, USA

Abstract

Two approaches are presented for the synthesis of the macrolide core of the mycolactone polyketides. The first intertwines ring closing metathesis (RCM) within a two-step Julia olefination protocol, while the second intercepts the optimized routes of Kishi, thereby providing formal access to the mycolactones.

Graphical abstract: Synthetic studies on the mycolactone core

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Article information

DOI
https://doi.org/10.1039/C0OB00540A
Article type
Paper
Submitted
03 Jun 2010
Accepted
17 Aug 2010
First published
19 Aug 2010

Org. Biomol. Chem., 2010,8, 5159-5165

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Synthetic studies on the mycolactone core

K. Ko, M. D. Alexander, S. D. Fontaine, J. E. Biggs-Houck, J. J. La Clair and M. D. Burkart, Org. Biomol. Chem., 2010, 8, 5159 DOI: 10.1039/C0OB00540A

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