Unprecedented 1,14-seco-Crotofolanes from Croton insularis: Oxidative Cleavage of Crotofolin C by a Putative Homo-Baeyer-Villiger Rearrangement

作者：Maslovskaya Lidiya A; Savchenko Andrei I; Pierce Carly J; Gordon Victoria A; Reddell Paul W; Parsons Peter G; Williams Craig M^*

来源：Chemistry - A European Journal, 2014, 20(44): 14226-14230.

DOI：10.1002/chem.201404250

• Baeyer-Villiger rearrangement
• crotofolin C
• Croton insularis
• natural products
• structure elucidation

EBC-162 isolated from Croton insularis, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolinC (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.

• 出版日期2014-10-27