Stereoselective Synthesis of
(4S,6S)-6-Hydroxy-4-undecanolide:
A Pheromone of the Giant White Butterfly Idea
leuconoe

Jhillu Singh Yadav; Poli Adi Narayana Reddy; Hissana Ather; Alleni Suman Kumar; Attaluri R. Prasad; Basi V. Subba Reddy; Ahmad Al Khazim

doi:10.1055/s-0031-1289671

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Synthesis 2012(4): 579-584
DOI: 10.1055/s-0031-1289671

PAPER

Stereoselective Synthesis of (4S,6S)-6-Hydroxy-4-undecanolide: A Pheromone of the Giant White Butterfly Idea leuconoe

Jhillu Singh Yadav*^a,b, Poli Adi Narayana Reddy^a, Hissana Ather^a, Alleni Suman Kumar^a, Attaluri R. Prasad^a, Basi V. Subba Reddy^a, Ahmad Al Khazim^b
^a Pheromone Group, Natural product Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in ;
^b Engineer Abdullah Baqshan for Bee Research, King Saudi University, Saudi Arabia

Further Information

Publication History

Received 11 October 2011
Publication Date:
16 January 2012 (online)

Abstract
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Abstract

The stereoselective synthesis of (4S,6S)-6-hydroxy-4-undecanolide, a major pheromone component in the secretion of Idea leuconoe has been accomplished employing Prins cyclization to produce anti-1,3-diols and hydroboration/oxidation of terminal olefin to introduce primary alcohol as the key steps.

Key words

pheromones - Prins cyclization - Mitsunobu inversion - anti-1,3-diol - chemoselective oxidation of 1,4-diols

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