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Communication | Special issue | Vol 30, No. 1, 1990, pp.311-316
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S49
■ Comformational Difference between Erythrinan- and Homoerythrinan-3-ones: Total Synthesis of (±)-Schelhammeridine and (±)-3-Epischelhammeridine

Yoshisuke Tsuda,* Shinzo Hosoi, and Masami Murata

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

Abstract

Erythrinan- and homoerythrinan-3-ones behave differently toward hydride reductions suggesting their conformational difference: for example, Δ1-erythrinan-3-one gives 3α-alcohol and Δ1-domoerythrinan-3-one gives 3β-alcohol stereoselectively on reduction with NaBH4-CeCl3 in methanol. Based on these observations, total syntheses of homoerythrinan alkaloids, schelhammeridine and 3-epischelhammeridine, and an erythrinan alkaloid, 8-oxoerysotrine, were accomplished.