(鈭?-(2S,3R,Z)-Nakinadine A: First Asymmetric Synthesis and Absolute Configuration Assignment
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- 作者：Stephen G. Davies ; Ai M. Fletcher ; Paul M. Roberts ; Rushabh S. Shah ; Amber L. Thompson ; James E. Thomson
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：March 7, 2014
- 年：2014
- 卷：16
- 期：5
- 页码：1354-1357
- 全文大小：441K
- 年卷期：v.16,no.5(March 7, 2014)
- ISSN：1523-7052
文摘
Mannich-type reaction of methyl phenylacetate with the N-tert-butylsulfinyl imine derived from (R)-tert-butylsulfinamide and (Z)-14-(pyridin-3鈥?yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (鈭?-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the absolute (2S,3R,Z)-configuration within the natural product. (鈭?-(2S,3R,Z)-Nakinadine A was prepared in 10 steps from 11-bromoundecan-1-ol, in 10% overall yield, 97:3 dr [(Z):(E) ratio], and >98% ee.