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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
Author(s) -
Guerriero Antonio,
D'Ambrosio Michele,
Pietra Francesco
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780606
Subject(s) - chemistry , allylic rearrangement , stereochemistry , archipelago , reactivity (psychology) , coral , organic chemistry , ecology , biology , catalysis , medicine , alternative medicine , pathology
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 analogue brianthein W ( 6 ), were isolated from the pennatulacean coral Funiculina quadrangularis (P ALLAS , 1766) collected in the Tuscan archipelago. 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.