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Communication | Regular issue | Vol 12, No. 11, 1979, pp.1463-1466
Published online, 1st January, 1970
DOI: 10.3987/R-1979-11-1463
Synthesis of (±)-9-Demethylpsychotrine and (±)-10-Demethylpsychotrine

Tozo Fujii,* Masashi Ohba, Satyesh C. Pakrashi, and Esahak Ali

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

The synthesis of (±)-9-demethylpsychotrine (I) has been achieved by an initial condensation of 3-benzyloxy-4-methoxyphenacyl bromide (Xa) with the lactim ether IX, derived from the lactam ester VIII, and the subsequent steps proceeding through the intermediates XIa, XIIa, XIIIc, XIIIa, XIVa, XVa, XVIa, XVIIa, and XVIIIa. A parallel synthesis starting with 4-benzyloxy-3-methoxyphenacyl bromide (Xb) and IX afforded (±)-10-demethylpsychotrine (II).