Thiopyran Route to Polypropionates:  An Efficient Synthesis of Serricornin

The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one], a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde (6) is described. The key steps include ena...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-11, Vol.71 (23), p.8989-8992
Main Authors: Ward, Dale E, Jheengut, Vishal, Beye, Garrison E
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Propionates - chemical synthesis
Propionates - chemistry
Pyrans - chemistry
Stereoisomerism
Sulfhydryl Compounds - chemistry
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Summary:The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one], a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4-one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole to fabricate the tetrapropionate skeleton, stereoselective Li s Bu3BH reduction of the resulting aldol adduct, Barton−McCombie deoxygenation, and Raney nickel desulfurization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061747w