Studies on the formation of a tricyclic C-2-symmetric sulfide

Attempts to synthesise chiral sulfide 1 from the dimesylate precursor 5, vi a a cyclisation reaction using sodium Sulfide in dimethyl sulfoxide, led to the unexpected formation of an unsymmetrical furan derivative 8. Studies w ere made into the effect of changing the leaving group. and changing the so lvent of reaction. The desired compound Could be synthesised in good fields from the xanthate 9 Using a radical-mediated procedure. (C) 2001 Elsevier Science Ltd. All rights reserved.