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Synthesis 2012(4): 579-584
DOI: 10.1055/s-0031-1289671
DOI: 10.1055/s-0031-1289671
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Synthesis of (4S,6S)-6-Hydroxy-4-undecanolide: A Pheromone of the Giant White Butterfly Idea leuconoe
Further Information
Received
11 October 2011
Publication Date:
16 January 2012 (online)
Publication History
Publication Date:
16 January 2012 (online)
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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