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Review | Regular issue | Vol 3, No. 11, 1975, pp.1005-1033
Published online, 1st January, 1970
DOI: 10.3987/R-1975-11-1005
Application of Lead Tetraacetate Oxidation to the Synthesis of Isoquinoline Alkaloids

Bunsuke Umezawa* and Osamu Hoshino

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


A variety of 7- or 6-tetrahydroisoquinolinols are readily oxidized with lead tetraacetate in acetic acid or methylene chloride to give p-quinol acetates or 4-acetates, whose acid treatment has produced (±)-aporphines, (±)-homoaporphines, (±)-homomorphinandienones, and (±)-homoproaporphines or (±)-isopavines, respectively.