GC-MS analysis of phytosterol profiles in dried morel mushrooms by our lab revealed the presence of several compounds not previously known to be found in mushrooms. However, one compound with a molecular weight of 396, thought to be ergosta-5,22,24(28)-trienol (1) has yet to be confirmed. Thus, the goal of this research was to synthesize 1 and obtain GC-MS data that proves the identity of the unknown compound. The synthesis of 1 begins with stigmasterol, which is converted in four steps using a literature method to the aldehyde (2). We anticipate that sequential Julia and Wittig reactions followed by hydrolysis of the acetate ester will afford 1. The Julia reagent proposed through the reaction of 2-mercaptobenzothiazole with 1-bromo-3-methyl-2-butanone (prepared by bromination of 3-methyl-2-butanone) to form the sulfide, 1-(benzo[d]thiazol-2-ylthio)-3-methylbutan-2-one (72% yield). This intermediate was then oxidized with mCPBA to produce the sulfone, 1-(benzo[d]thiazol-2-ylsulfonyl)-3-methyl-2-butanone (3) (19% yield).

Synthesis of ergosta-5,22,24(28)-trienol

255th National Meeting (2018)

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