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Communication | Regular issue | Vol 4, No. 2, 1976, pp.235-240
Published online, 1st January, 1970
DOI: 10.3987/R-1976-02-0235
Biomimetic Synthesis of the Dibenzazonine Alkaloid Laurifonine

S. Morris Kupchan,* Chang-Kyu Kim, and Katsuji Miyano

*Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, U.S.A.

Abstract

A facile and efficient biomimetic synthesis of laurifonine (9a) is described. Reduction of (±)-O-methylflavinantine (5a) with sodium borohydride yielded a mixture of the epimeric dienols 6a, in 83% yield. Treatment of the dienol mixture with boron trifluoride-etherate followed by hydrogenation over platinum in methanol gave laurifonine (%, 81%). When a mixture of (±)-proerythrinadienols (2a) was subjected to acid-catalyzed rearrangement, the (±)-desoxyaporphine 4 was obtained, in 85% yield. Possible biogenetic implications of the observations are discussed.