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Communication | Regular issue | Vol 23, No. 3, 1985, pp.567-569
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0567
A Modified Synthesis of the (+)-8α-phenylsulfonyl-des-AB-cholestane via an Intramolecular Nucleophilic Attack to Epoxide — A Total Synthesis of Vitamine D3

Hideo Nomoto, Hiroshi Kurobe, Keiichiro Fukumoto,* and Tetsuji Kametani

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


An intramolecular alkylation of the phenylsulfonyl epoxide (6), which was readily obtained from the aldehyde (5), gave a separable mixture of the alcohols (7a) and (8a). The alcohol (8a) was then dehydrated via the corresponding mesylate (8b) to afford the olefin (9) which on hydrogenation furnished (+)-8α-phenylsulfonyl-des-AB-cholestane (1). Further this product was converted into vitamin D3 (4).