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Communication | Regular issue | Vol 41, No. 3, 1995, pp.425-429
Published online, 1st January, 1970
DOI: 10.3987/COM-94-7001
Concise Enantioselective Synthesis of (+)-Asperlin by Application of the Sharpless Kinetic Resolution to 2-Furylmethanol Derivatives Bearing Alkenyl Moiety on the Side Chain

Toshio Honda*, Nobuko Sano, and Kazuo Kanai

*Institute of Medicinal Chemistry, Hoshi University, Ebara 2-4-41, Shinagawa, Tokyo 142, Japan


A reaction of (±)-(E)-1-(2-furyl)but-2-en-1-ol (1) under the Sharpless asymmetric oxidation condition using 30 mol% of D-(-)-diisopropyl tartrate (DIPT), 25 mol% of titanium tetraisopropoxide and 120 mol% of tert-butyl hydroperoxide (TBHP) afforded the (S)-epoxide (3), in 42% yield with high optical purity, which was further converted into an antitumour antibiotic, asperlin (10).