Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones.

Abstract

Ruthenium (IV) dioxide dihydrate in fluoro acid medium was found to be a very efficient agent for the oxidative coupling of non phenolic lignans and their derivatives, and this method was applied to the total synthesis of (+/-)-neoisostegane 2a and (+/-)-steganolide A 2b. This procedure was also used to obtain the first stereospecific synthesis of a cis-bisbenzocyclooctadiene lactone, the (+/-)-deoxyschizandrin 17, of which, was afforded by a short reduction sequence.