(-)-(3R,4R)-3-Butyl-4-vinylcyclopentene [(-)-1] was synthesized via ()-(1S,5R)-3-oxabicyclo [3,3,0] oct-6-en-2-one. Synthetic (-)-1 coincid
ed with the peak with later retention time of racemic (+/-)-1 in a chi
ral GC (CP-Cyclodex 236M), while the natural 1 in essential oils from
the marine brown algae, Dictyopteris prolifera and D. sp. was identica
l with the earlier retention time peak. Thus, the absolute configurati
on of the natural product in Dictyopteris oils was determined as (+)-(
3S,4S) with ca 100% enantiomeric excess. (C) 1997 Elsevier Science Ltd
.