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Synthesis 2011(8): 1279-1282  
DOI: 10.1055/s-0030-1258458
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Stereoselective Total Synthesis of Synargentolide A from 3,4,6-Tri-O-acetyl-d-glucal

Gowravaram Sabitha*, S. Siva Sankara Reddy, Atla Raju, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
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Publication History

Received 31 December 2010
Publication Date:
03 March 2011 (online)

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Abstract

A short and highly stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone synargentolide A is described from the chiral starting material 3,4,6-tri-O-acetyl-d-glucal. Key steps of the synthesis are lactol opening, Brown’s asymmetric allylation, and a ring-closing metathesis (RCM) reaction.

Key words

3,4,6-tri-O-acetyl-d-glucal - δ-lactones - synargento­lide - Brown’s allylation - RCM