Unknown

Dataset Information

0

Alternative synthesis of the Colorado potato beetle pheromone.


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.

SUBMITTER: Faraldos JA 

PROVIDER: S-EPMC3863329 | BioStudies | 2013-01-01

REPOSITORIES: biostudies

Similar Datasets

2015-01-01 | S-EPMC4623779 | BioStudies
2019-01-01 | S-EPMC6776033 | BioStudies
2018-01-01 | S-EPMC5890793 | BioStudies
2020-01-01 | S-EPMC7142049 | BioStudies
1000-01-01 | S-EPMC4673573 | BioStudies
2020-01-01 | S-EPMC7551256 | BioStudies
2011-01-01 | S-EPMC3149374 | BioStudies
2014-01-01 | S-EPMC4036322 | BioStudies
2013-01-01 | S-EPMC3763493 | BioStudies
1000-01-01 | S-EPMC6271342 | BioStudies