Unprecedented 1, 14‐seco‐Crotofolanes from Croton insularis: Oxidative Cleavage of Crotofolin C by a Putative Homo‐Baeyer–Villiger Rearrangement. Issue 44 (18th September 2014)

• Record Type: Journal Article
• Authors: Maslovskaya, Lidiya A.; Savchenko, Andrei I.; Pierce, Carly J.; Gordon, Victoria A.; Reddell, Paul W.; Parsons, Peter G.; Williams, Craig M.
• Is Part Of: Chemistry. Volume 20:Issue 44(2014)
• Page Start: 14226
• Page End: 14230
• Publication Date: 2014-09-18
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201404250
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>EBC‐162 isolated from <italic>Croton insularis</italic>, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C (<bold>4</bold>). 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‐<italic>seco</italic>‐crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented.</p> </abstract>