BIS-ALLYLIC REACTIVITY OF THE FUNICOLIDES, 5,8(17)-DIUNSATURATED BRIARANE DITERPENES OF THE SEA PEN FUNICULINA-QUADRANGULARIS FROM THE TUSCAN ARCHIPELAGO, LEADING TO 16-NORTAXANE DERIVATIVES

Authors
GUERRIERO A DAMBROSIO H PIETRA F
Citation
A. Guerriero et al., BIS-ALLYLIC REACTIVITY OF THE FUNICOLIDES, 5,8(17)-DIUNSATURATED BRIARANE DITERPENES OF THE SEA PEN FUNICULINA-QUADRANGULARIS FROM THE TUSCAN ARCHIPELAGO, LEADING TO 16-NORTAXANE DERIVATIVES, Helvetica Chimica Acta, 78(6), 1995, pp. 1465-1478
Citations number
38
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
78
Issue
6
Year of publication
1995
Pages
1465 - 1478
Database
ISI
SICI code
0018-019X(1995)78:6<1465:BROTF5>2.0.ZU;2-T
Abstract
Funicolides A-C (1-3), D (5), and E (7) and 7-epifunicolide A (4), new 5,8(17)-diunsaturated briarane diterpenes, as well as the known analo gue brianthein W (6), were isolated from the pennatulacean coral Funic ulina quadrangularis (PALLAS, 1766) collected in the Tuscan archipelag o. Easy degradation under oxidative and/or basic conditions served to assign the ester groups at C(2) or C(14), while revealing bis-allylic reactivity at C(7) with formation of 16-nortaxane derivatives.