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Synthesis 2005(14): 2341-2344  
DOI: 10.1055/s-2005-870025
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© Georg Thieme Verlag Stuttgart · New York

Convenient Synthesis of Volatile Streptomyces Lactones

Chandan P. Amonkara, Santosh G. Tilve*a, P. S. Parameswaranb
a Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India
Fax: +91(832)245184; e-Mail: santoshtilve@yahoo.com;
b Chemical Oceanography Division, National Institute of Oceanography (CSIR), Dona-Paula-Goa 403 004, India
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Publication History

Received 20 January 2005
Publication Date:
14 July 2005 (online)

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Abstract

A convenient three-step synthetic approach towards 3-alkyl-5-methyl-2[5H]furanones is described. The steps involved in the synthesis are domino primary alcohol oxidation-Wittig reaction, acid-catalysed lactonisation and isomerisation. This synthetic approach has been exploited to synthesise four Streptomyces lactones.

Key words

domino reaction - Wittig reaction - isomerisation - lactone - oxidation