Dysoxysulfone

Trithiolane is attacked at one of the disulfide sulfur atoms with methyl lithium at — 78 "C. The resulting ring-opened intermediate can be quenched with an electrophile as in the synthesis of dysoxysulfone (103) (Scheme 25) <94JOC2273>. 

C2H4S5, Mr 188.35, cryst., mp. 60-61 °C. L. is a component of the East Asian edible mushroom shiitake (Lentinus edodes, Basidiomycetes) and, together with the polythiepanes and 1,2,4-trithioIane shown in the formula scheme, is responsible for the characteristic odor of the mushroomPrecursors of this flavor substance are 2,4,5,7-tetrathiaoctane 2,2,7,7-tetraoxide and 2,3,5,7,9-pentathiadecane 9,9-dioxide (SE-3), the structures of which were confirmed by synthesis (see also dysoxysulfone). The cyclic flavor substances can be prepared simply by reaction of dichloromethane with NajSj.s (from NajS and sulfur)Shiitake mushrooms - cultivated on dead wood - are becoming increasingly popular in Europe and North America on account of their excellent flavor. L. is also found as a volatile component of cooked mutton and in the alga Chondria californica. ... 

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