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Communication | Regular issue | Vol 16, No. 11, 1981, pp.1947-1950
Published online, 1st January, 1970
DOI: 10.3987/R-1981-11-1947
■ Alternative Syntheses of (±)-Epi- and (±)-Desethyl-ibogamine Using a Diels-Alder Reaction of 1-Benzyl-2(1H)-pyridone

Hiroshi Tomisawa,* Hiroshi Hongo, Hideki Kato, Kumi Sato, and Reiko Fujita

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

The Diels-Alder reaction of 1-benzyl-2(1H)-pyridone (1) with methyl acrylate (2) gave methyl 2-benzyl-3-oxo-2-azabicyclo[2.2.2]oct-7-ene-6-endo-carboxylate (3) as a main product. Using this compound a short total synthesis of (±)-epi-ibogamine was achieved. (±)-Desethylibogamine was also synthesized formally from the Diels-Alder adduct (11) of 1 with maleic anhydride.