title: Unprecedented 1,14-seco-crotofolanes from Croton insularis: oxidative cleavage of crotofolin C by a putative homo-Baeyer-Villiger rearrangement.
abstract: 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.
authors.affiliation: QIMR Berghofer Medical Research Institute, PO Royal Brisbane Hospital, Brisbane, 4029, Queensland (Australia).
authors.forename: Lidiya A
authors.initials: LA
authors.lastname: Maslovskaya
authors.forename: Andrei I
authors.initials: AI
authors.lastname: Savchenko
authors.forename: Carly J
authors.initials: CJ
authors.lastname: Pierce
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Gordon
authors.forename: Paul W
authors.initials: PW
authors.lastname: Reddell
authors.forename: Peter G
authors.initials: PG
authors.lastname: Parsons
authors.forename: Craig M
authors.initials: CM
authors.lastname: Williams
mesh_terms: D029802:Croton / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D004224:Diterpenes; D010936:Plant Extracts
keywords: Baeyer-Villiger rearrangement; Croton insularis; crotofolin C; natural products; structure elucidation