N,N-Acetals as N-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide
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- 作者：Marloes A. Wijdeven ; Roel Wijtmans ; Rutger J. F. van den Berg ; Wim Noorduin ; Hans E. Schoemaker ; Theo Sonke ; Floris L. van Delft ; Richard H. Blaauw ; Richard W. Fitch ; Thomas F. Spande ; John W. Daly ; Fl
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：September 18, 2008
- 年：2008
- 卷：10
- 期：18
- 页码：4001-4003
- 全文大小：125K
- 年卷期：v.10,no.18(September 18, 2008)
- ISSN：1523-7052
文摘
A stereoselective synthesis of (+)-epiquinamide is presented in combination with determination of the absolute configuration of the natural product. Key steps in the sequence involved chemoenzymatic formation of an enantiomerically pure cyanohydrin, reductive cyclization to the corresponding cyclic N,N-acetal, and subsequent conversion into a suitable N-acyliminium ion precursor to enable construction of the second ring.