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Review | Regular issue | Vol 27, No. 4, 1988, pp.1009-1033
Published online, 1st January, 1970
DOI: 10.3987/REV-87-376
Chiral Syntheses of Benzo[a]quinolizidine-type Alangium Alkaloids

Tozo Fujii,* Masashi Ohba, and Shigeyuki Yoshifuji

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

Abstract

Nineteen benzo[a]quinolizidine alkaloids isolated so far from Alangium plants are structurally classified into four types (I-IV), and studies on chiral syntheses of these I-IV-type alkaloids are reviewed with particular emphasis on the synthetic strategies and tactics employed. It has been found that chiral syntheses of all of these types of alkaloids are possible through the “cincholoiponincorporating route” or the “lnctim ether route”, and the absolute configurations of four II-type, two III-type, and one IV-type alkaloids have been established by such syntheses. An extension of the “lactim ether route” to the synthesis of (-)-ochropposinine [(-)-99g] has unequivocally established the absolute stereochemistry of this Ochrosia alkaloid.