Synthesis of bridged analogs of epibatidine. 3-chloro-5,7,8,9,9a,10-hexahydro-7,10-methanopyrrolo[1,2-b]-2,6-naphthyr idine and 2-chloro-5,5a,6,7,8,10-hexahydro-5,8-methanopyrrolo[2,1-b]-1,7-naphthyri dine

F. Ivy Carroll; S. Mascarella; Hernan A. Navarro; Lawrence E. Brieaddy; Lawrence E. Brieaddy; S. Wayne Mascarella; Hernan A. Navarro; Robert Atkinson; MI Damaj; BR Martin; Ivy Carroll

Synthesis of bridged analogs of epibatidine. 3-chloro-5,7,8,9,9a,10-hexahydro-7,10-methanopyrrolo[1,2-b]-2,6-naphthyr idine and 2-chloro-5,5a,6,7,8,10-hexahydro-5,8-methanopyrrolo[2,1-b]-1,7-naphthyri dine

Brieaddy, L., Mascarella, S., Navarro, H., Atkinson, R., Damaj, MI., Martin, BR., & Carroll, F. (2001). Synthesis of bridged analogs of epibatidine. 3-chloro-5,7,8,9,9a,10-hexahydro-7,10-methanopyrrolo[1,2-b]-2,6-naphthyr idine and 2-chloro-5,5a,6,7,8,10-hexahydro-5,8-methanopyrrolo[2,1-b]-1,7-naphthyri dine. Tetrahedron Letters, 42(23), 3795-3797.

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Abstract

The synthesis of conformationally locked analogs of epibatidine are described in which the key step is an intramolecular reductive palladium-catalyzed Heck-type coupling. (C) 2001 Elsevier Science Ltd. All rights reserved