Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus  Halichondria

Mudianta, Wayan; Katavic, Peter L; Lambert, Lynette K; Hayes, Patricia Y; Banwell, Martin; Munro, Murray HG; Bernhardt, Paul; Garson, Mary J

Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria

Date

2010

Authors

Mudianta, Wayan

Katavic, Peter L

Lambert, Lynette K

Hayes, Patricia Y

Banwell, Martin

Munro, Murray HG

Bernhardt, Paul

Garson, Mary J

Publisher

Elsevier

Abstract

Chemical analysis of an Indonesian sponge sample has provided three new 3-alkylpiperidine alkaloids, tetradehydrohaliclonacyclamine A, its mono-N-oxide derivative, and a 2-epi isomer. The absolute structure of tetradehydrohaliclonacyclamine A has been established by X-ray crystallography from anomalous dispersion effects using Cu radiation, which determined that the absolute configuration is 2S, 3S, 7S, 9S while an HPLC study revealed that the alkaloid is enantiomerically pure.