(2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a new amino alcohol from the caribbean sponge Haliclona vansoesti.

Abstract

The Caribbean marine sponge Haliclona vansoesti was found to contain a high amount (5% dry wt) of a new analogue of 4-sphingenine, (2R,3R, 7Z)-2-aminotetradec-7-ene-1,3-diol (1). Its structure was determined by detailed spectroscopic analysis. The relative configuration was deduced from the NMR data of the corresponding acetonide 5, while the absolute configuration was secured via protection of the primary alcohol and amino groups, and esterification of the secondary alcohol with Mosher's reagent.