Issue 3, 2011
From the journal:

Organic & Biomolecular Chemistry

Efficient total synthesis of (−)-stemoamide†

Toshio Honda,*a   Tomoha Matsukawaa  and  Kazunori Takahashia  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo, Japan
E-mail: honda@hoshi.ac.jp
Fax: +81-3-5498-5791
Tel: +81-3-5498-5791

Abstract

An efficient diastereoselective synthesis of (−)-stemoamide has been accomplished from a pyroglutamic acid derivative in eight steps and with 24% overall yield. The synthesis features an intramolecular samarium diiodide-promoted 7-exo-trigcyclization of a ketyl radical generated from the corresponding aldehyde.

Graphical abstract: Efficient total synthesis of (−)-stemoamide

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Article information

DOI
https://doi.org/10.1039/C0OB00850H
Article type
Communication
Submitted
08 Oct 2010
Accepted
19 Nov 2010
First published
03 Dec 2010

Org. Biomol. Chem., 2011,9, 673-675

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Efficient total synthesis of (−)-stemoamide

T. Honda, T. Matsukawa and K. Takahashi, Org. Biomol. Chem., 2011, 9, 673 DOI: 10.1039/C0OB00850H

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