Synthesis of a novel N-hydroxypyrrolidine using enzyme catalysed asymmetric carbon-carbon bond synthesis

被引:31
作者
Humphrey, AJ [1 ]
Parsons, SF [1 ]
Smith, MEB [1 ]
Turner, NJ [1 ]
机构
[1] Univ Edinburgh, Edinburgh Ctr Prot Technol, Dept Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
基金
英国生物技术与生命科学研究理事会;
关键词
imino sugars; transketolase; asymmetric carbon-carbon bond synthesis;
D O I
10.1016/S0040-4039(00)00645-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Hydroxypyrrolidine 5 has been prepared in nine steps starting from;3-O-benzylglyceraldehyde 13. The synthetic route employs Escherichia coli transketolase mediated C-C bond synthesis to establish the absolute stereochemistry and a subsequent ring contraction of a 1,2-oxazine 17 to provide the N-hydroxypyrrolidine nucleus. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4481 / 4485
页数:5
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