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

Atul K. Hajare; Laxmikant S. Datrange; Y. L. N. Murthy; Debnath Bhuniya; D. Srinivasa Reddy

doi:10.1055/s-0030-1258451

PAPER

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

Atul K. Hajare^a,b, Laxmikant S. Datrange^a, Y. L. N. Murthy^b, Debnath Bhuniya^a, 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;

Abstract

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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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References

Advinus Publication No.: ADV-A-010.

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