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EBC‐219: A New Diterpene Skeleton, Crotinsulidane, from the Australian Rainforest Containing a Bridgehead Double Bond
Author(s) -
Maslovskaya Lidiya A.,
Savchenko Andrei I.,
Krenske Elizabeth H.,
Pierce Carly J.,
Gordon Victoria A.,
Reddell Paul W.,
Parsons Peter G.,
Williams Craig M.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310923
Subject(s) - diterpene , stereochemistry , olefin fiber , chemistry , skeleton (computer programming) , amazon rainforest , rainforest , botany , biology , organic chemistry , anatomy , ecology , polymer
EBC‐219 ( 4 ), isolated from Croton insularis (Baill), was established by spectroscopic and DFT methods as the first member of a new diterpene skeletal class, uniquely defined by the presence of a bicyclo[10.2.1] bridgehead olefin. The proposed biogenetic pathway to 4 from the co‐isolated natural products EBC‐131 ( 1 ), EBC‐180 ( 2 ) and EBC‐181 ( 3 ) is highly likely. EBC‐180 ( 2 ) and EBC‐181 ( 3 ) showed moderate to strong cytotoxic activity against various cancer cell lines.