A Practical Synthesis of a Chiral Analogue of FTY720

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• 作者：Xinglong Jiang ; Baoqing Gong ; Kapa Prasad ; Oljan Repi
• 刊名：Organic Process Research & Development
• 出版年：2008
• 出版时间：November 21, 2008
• 年：2008
• 卷：12
• 期：6
• 页码：1164-1169
• 全文大小：154K
• 年卷期：v.12,no.6(November 21, 2008)
• ISSN：1520-586X

文摘

A practical synthesis of 1 involving a catalytic enantioselective construction of the quaternary carbon from imine 10 (derived from 13 and 14) and alkyl iodide 5 using Maruoka’s chiral catalyst 11 is described. This asymmetric alkylation followed by hydrolysis to amino acid 9 was accomplished in good yield with high chemical purity (>98%) and chiral purity (>96% ee). The improved synthesis enabled production of 1 in seven chemical steps (six isolations) in an overall yield of 22%.