M. D'Ambrosio, A. Guerriero, F. Pietra
May 6, 1987
Citations
0
Influential Citations
9
Citations
Journal
Helvetica Chimica Acta
Abstract
The Mediterranean alcyonacean Alcyonium (=Parerythropodium) coralloides (Pallas, 1766) is shown to contain the novel eudesmane sesquiterpenoids coralloidin C (=(–)−(4R,10S)-eudesma-5,7(11)-dien-15-yl acetate; (–)−4), coralloidin D (=(–)−(10R*)-eudesma-4,7(11)-diene-12,13-diyl diacetate; (–)−7), and coralloidin E (=(+)−(4R*,10R*)-eudesma-5,7-dien-11-ol;(+)−8). The absolute configuration of (–)−4 is derived by the exciton-coupling method, applied to deacetylcoralloidin Cp-anisate ((–)−6). Coralloidin E((+)−8), being also obtained on treatment of deacetylcoralloidin A (=(+)−(4R*, 8R*, 10R*)-eudesma-5,7(11)-dien-8-ol; (+)−2) with (COCl)2 in DMSO, is configurationally correlated to coralloidin A (=(+)−(4R*, 8R*, 10R*)-eudesma-5,7(11)-dien-8-yl acetate; (+)−1). Under acidic conditions, (+)−2 undergoes a complex rearrangement giving (+)-(3R*, 4S*, 5R*, 6R*, 7S*)-arist-10-(1)-en -3-ol ((+)−9), which is also obtained, together with (+)−8, on attempts to mesylate (+)−2.