A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir
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- 作者：Manuel Peifer ; Rapha毛lle Berger ; Valerie W. Shurtleff ; Jay C. Conrad ; David W. C. MacMillan
- 刊名：Journal of the American Chemical Society
- 出版年：2014
- 出版时间：April 23, 2014
- 年：2014
- 卷：136
- 期：16
- 页码：5900-5903
- 全文大小：409K
- 年卷期：v.136,no.16(April 23, 2014)
- ISSN：1520-5126
文摘
An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective 伪-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.