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Synthesis 2011(7): 1067-1070  
DOI: 10.1055/s-0030-1258451
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Enantiospecific Route to (+)-(1R,3S)-cis-Chrysanthemic Acid from (-)-d-Pantolactone [¹]

Atul K. Hajarea,b, Laxmikant S. Datrangea, Y. L. N. Murthyb, Debnath Bhuniyaa, D. Srinivasa Reddy*a,c
a Discovery Chemistry, Advinus Therapeutics Ltd., Quantum Towers, Plot No. 9, Rajiv Gandhi Infotech Park, Phase-I, Hinjewadi, Pune 411057, India
b Department of Organic Chemistry, Andhra University, Visakhapatnam 530003, India
c Present address: , National Chemical Laboratory (CSIR, India), Division of Organic Chemistry, Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India
Fax: +91(20)66539620; e-Mail: ds.reddy@ncl.res.in; e-Mail: dsreddy88@yahoo.com;
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Publication History

Received 3 December 2010
Publication Date:
01 March 2011 (online)

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Abstract

In this paper, a novel route for the synthesis of (+)-(1R,3S)-cis-chrysanthemic acid is described. The use of readily available (-)-d-pantolactone as a starting point, application of ring-closing metathesis to form the cyclopentene intermediate, and Haller-Bauer/Grob-type fragmentation to form the target compound are the highlights of the present synthesis.

Key words

ring closure - stereoselective synthesis - Wittig reaction - alkenes - metathesis

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Advinus Publication No.: ADV-A-010.

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Advinus Publication No.: ADV-A-010.