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

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-aminot etradec-7-ene-1,3-diol (1). Its structure was determined by detailed spectr oscopic analysis. The relative configuration was deduced from the NMR data of the corresponding acetonide 5, while the absolute configuration was secu red via protection of the primary alcohol and amino groups, and esterificat ion of the secondary alcohol with Mosher's reagent.