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Paper | Regular issue | Vol 48, No. 10, 1998, pp.2089-2093
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8259
Aaptosamine, a New 5,8-Diazabenz[cd]azulene Alkaloid from the Caribbean Sponge Aaptos aaptos. An Unprecedented Base-catalyzed Rearrangement of 9-Demethyloxyaaptamine

Winston F. Tinto

*Laboratory of Bioorganic Chemistry, Department of Biological Chemical Sciences, University of the West Indies, Cave Hill Campus, P.O. Box 64, Bridgetown, Barbados, West Indies

Abstract

A new 5,8-diazabenz[cd]azulene alkaloid, aaptosamine, was isolated from the marine sponge Aaptos aaptos collected in the southern Caribbean. The structure was determined by 2D NMR spectroscopy using HMQC and HMBC experiments. The known alkaloid 9-demethyloxyaaptamine which was isolated from an earlier collection of A. aaptos, underwent an unprecedented base-catalyzed rearrangement to give a new furanonaphthyridine derivative.