Biomimetic Synthesis of Equisetin and (+)‐Fusarisetin A. Issue 39 (12th August 2013)

• Record Type: Journal Article
• Authors: Yin, Jun; Kong, Lili; Wang, Cheng; Shi, Yingbo; Cai, Shujun; Gao, Shuanhu
• Is Part Of: Chemistry. Volume 19:Issue 39(2013)
• Page Start: 13040
• Page End: 13046
• Publication Date: 2013-08-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201302163
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>(+)‐Fusarisetin A belongs to a group of acyl tetramic acid natural products that show potential anticancer activity. Equisetin, a biogenetically related acyl tetramic acid, contains the basic skeleton of (+)‐fusarisetin A. We proposed that equisetin and (+)‐fusarisetin A share a biosynthetic pathway that starts with naturally occurring (<italic>S</italic>)‐serine and an unsaturated fatty acid. In support of this hypothesis, we have demonstrated that a cyclization sequence involving an intramolecular Diels–Alder reaction followed by a Dieckmann cyclization of polyenoylamino acid yielded equisetin. The aerobic oxidation of equisetin, promoted by either Mn^III/O₂ or a reactive oxygen species (ROS) produced by visible‐light chemistry, gave peroxyfusarisetin, which could be easily reduced to (+)‐fusarisetin A. We report herein detailed information on the biogenetic synthesis of equisetin and (+)‐fusarisetin A.</p> </abstract>