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Paper | Regular issue | Vol 32, No. 2, 1991, pp.319-328
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5652
Quinolizidines. XXIX. Preparation of (-)-Dihydrocorynantheol

Masashi Ohba, Takako Ohashi, and Tozo Fujii*

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


An alternative, total synthesis of the indoloquinolizidine alkaloid (-)-dihydrocorynantheol [(-)-1], adaptable to that on a gram scale preparation, has been achieved via a "lactim ether route". The route started with an initial condensation between the lactim ether [(+)-4] and 3-(chloroacetyl)indole and proceeded through the lactam ketone [(+)-5], oxazolium salt (6), N-substituted lactam [(+)-8], quaternary iminium salt (9), and tetracyclic ester [(-)-11].