Submitted to: Tetrahedron Asymmetry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 31, 1998
Publication Date: N/A
Interpretive Summary: The sex pheromones of a number of important moths are optically active epoxides whose biological activities may be critically impaired by even small amounts of their mirror images. As a result, highly precise synthetic methodology has to be employed when preparing such compounds to ensure enantiomeric impurity of synthetic intermediates. This manuscript describes sa new procedure for synthesizing chiral epoxides wherein the critical three-dimensional unit is derived from a defined structure (the readily available sugar mannitol) and elaborated into a versatile four-carbon unit that will be useful for various syntheses.
1-(Trichloromethyl)-1,2-glycols were converted to 2,3-epoxycarboxylic acids with 100% stereoselectivity. Threo-glycols afforded cis-epoxides, while erythro-gycols preovided the trans-isomers.