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Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization
Journal article   Peer reviewed

Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization

Barry B Snider, Jane Y Kiselgof and Bruce M Foxman
Journal of organic chemistry, Vol.63(22), pp.7945-7952
10/01/1998
DOI: https://doi.org/10.1021/jo981238x

Abstract

Alcohols Organic compounds Anions Cyclization Oxidation Manganese Chemical Synthesis Organic Chemistry
Tetraene 1 was prepared in nine steps from the known propargylic alcohol 7 in 17% overall yield or as a 2:1 E/Z mixture in only five steps in 7% overall yield. Oxidative cyclization of 1 with 2 equiv of Mn(OAc)3·2H2O and 1 equiv of Cu(OAc)2 in MeOH at 25 °C provided 35% of tetracycle 2. Further elaboration provided (±)-isosteviol (3) in six steps in 51% yield and (±)-beyer-15-ene-3β,19-diol in four steps in 17% yield.

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