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Paper | Special issue | Vol 39, No. 1, 1994, pp.101-116
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S(B)3
An Approach to Open Chain and Modified Heterocyclic Analogues of the Acetylcholine-sterase Inhibitor, Huperzine A, through a Bicyclo[3.3.1]nonane Intermediate

Alan P. Kozikowski, Giuseppe Campiani, and Werner Tückmantel*

*Mayo Foundation for Medical Education and Research, 4500 San Pablo Road, Jacksonville, FL 32224, USA


The use of the bicyclo[3.3.1]nonane derived keto urethane (3) in a general synthesis of open chain and modified heterocyclic analogues of huperzine A was investigated and resulted in the preparation of the dimethylcarbamoyloxy analogue (27). Thiazole annulation by the Gewald procedure gave only the undesired regioisomer (36).