Unprecedented 1,14‐seco‐Crotofolanes from Croton insularis: Oxidative Cleavage of Crotofolin C by a Putative Homo‐Baeyer–Villiger Rearrangement |
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| Authors: | Dr Lidiya A Maslovskaya Dr Andrei I Savchenko Carly J Pierce Dr Victoria A Gordon Dr Paul W Reddell Prof Peter G Parsons Prof Craig M Williams |
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| Institution: | 1. QIMR Berghofer Medical Research Institute, PO Royal Brisbane Hospital, Brisbane, 4029, Queensland (Australia);2. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072 (Australia);3. EcoBiotics Limited, PO Box 1, Yungaburra, 4884, Queensland (Australia) |
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| 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. |
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| Keywords: | Baeyer– Villiger rearrangement crotofolin C Croton insularis natural products structure elucidation |
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