Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

被引:85
作者
Sánchez-Sancho, FS [1 ]
Herradón, B [1 ]
机构
[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
D O I
10.1016/S0957-4166(98)00178-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The kinetic resolutions of both (+/-)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(+/-)-5] and (+/-)-N(tert-butoxycarbonyi)-2-(hydroxymethyl)piperidine [(+/-)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)-6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2-4 steps) and proceeded with satisfactory overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:1951 / 1965
页数:15
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