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Unprecedented 1,14‐ seco ‐Crotofolanes from Croton insularis : Oxidative Cleavage of Crotofolin C by a Putative Homo‐Baeyer–Villiger Rearrangement
Author(s) -
Maslovskaya Lidiya A.,
Savchenko Andrei I.,
Pierce Carly J.,
Gordon Victoria A.,
Reddell Paul W.,
Parsons Peter G.,
Williams Craig M.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404250
Subject(s) - oxidative cleavage , stereochemistry , chemistry , natural product , cleavage (geology) , oxidative phosphorylation , biology , organic chemistry , biochemistry , catalysis , paleontology , fracture (geology)
EBC‐162 isolated from Croton insularis , obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C ( 4 ). Novel oxidative degradation products, EBC‐233 and EBC‐300, which are the first crotofolane endoperoxides, were also isolated. Both endoperoxides were found to be stable intermediates, which are proposed to undergo an unprecedented homo‐Baeyer–Villiger biosynthetic rearrangement to give a new class of 1,14‐ seco ‐crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented.