Exploring the Original Proposed Biosynthesis of (+)-Symbioimine: Remote Exocyclic Stereocontrol in a Type I IMDA Reaction

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• 作者：Jason P. Burke ; Michal Sabat ; Diana A. Iovan ; William H. Myers ; Jason J. Chruma
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：July 16, 2010
• 年：2010
• 卷：12
• 期：14
• 页码：3192-3195
• 全文大小：241K
• 年卷期：v.12,no.14(July 16, 2010)
• ISSN：1523-7052

文摘

The originally proposed biosynthesis of (+)-symbioimine was explored, resulting in the successful intramolecular Diels−Alder (IMDA) cyclization of an appropriate (E,E,E)-1,7,9-decatrien-3-one. In contrast to the originally proposed biosynthesis, the IMDA reaction appears to proceed via an endo transition state. Remarkably, a single exocyclic stereogenic center effectively controls the π-facial selectivity affording a highly diastereoselective cycloaddition.