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Paper | Regular issue | Vol 41, No. 11, 1995, pp.2575-2585
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7224
Structural and Conformational Analysis of Naturally Occurring Cularine N-Oxide Alkaloids

Rafael Suau,* Rafael Garcia Segura, M. Victoria Silva, Maria Valpuesta, Domingo Dominguez, and Luis Castedo

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, E-29071 Málaga, Spain

Abstract

(+)-cis- and (+)-trans-Cularidine N-oxides were isolated from Ceratocapnos heterocarpa. Their structures and conformations were derived from 1H, 13C, one dimensional nOe nmr data and their chemical behaviour. The trans isomer possesses the usual conformation of cularine alkaloids and readily undergoes Cope elimination. The cis isomer exhibits a different conformation at the dihydroxepine ring.