Alternative synthesis of the Colorado potato beetle pheromone

Faraldos, Juan A., Coates, Robert M. and Giner, José-Luis 2013. Alternative synthesis of the Colorado potato beetle pheromone. Journal of Organic Chemistry 78 (20) , pp. 10548-10554. 10.1021/jo4017056

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Abstract

A concise preparation of the pheromone secreted by the male Colorado potato beetle [viz. (3S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one] was accomplished in four steps starting from 2-fluoronerol or 2-fluorogeraniol. The key step in the synthesis involves a 6-endo epoxide ring-opening with ester participation that simultaneously inverts the 3R-configuration of the (3R)-2,3-epoxy-2-fluoroprenyl acetate intermediate and installs the ketone functionality of the semiochemical. Extensive NMR studies validate the proposed 6-endo mechanism of the featured rearrangement, which under anhydrous conditions resulted in the formation of two bicyclic 1,3-dioxan-5-ones via an unprecedented intramolecular Prins cyclization.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	ACS
ISSN:	0022-3263
Last Modified:	23 Mar 2017 03:34
URI:	https://orca.cardiff.ac.uk/id/eprint/70956

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