A practical synthesis of a chiral analogue of FTY720

…, B Gong, K Prasad, O Repič

Index: Jiang, Xinglong; Gong, Baoqing; Prasad, Kapa; Repic, Oljan Organic Process Research and Development, 2008 , vol. 12, # 6 p. 1164 - 1169

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Citation Number: 19

Abstract

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 ...

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