An efficient asymmetric synthesis of the mercaptopyrrolidine side chain of an important beta-methyl carbapenem antibiotic

被引：8

作者：

Armstrong, JD

Keller, JL

Lynch, J

Liu, T

Hartner, FW

Ohtake, N

Okada, S

Imai, Y

Okamoto, O

Ushijima, R

Nakagawa, S

Volante, RP

机构：

[1] Department of Process Research, Merck Research Laboratories, Merck and Co., Inc., Rahway, NJ 07065

[2] Drug Discovery Research Laboratories, Tsukuba Research Institute, Banyu Pharmaceutical Co., Ltd., Tsukuba 300-33

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(97)00613-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric synthesis of the mercaptopyrrolidine side chain 2 Is described The beta-ketoester 4 is hydrogenated diastereoselectively to give the (R)-beta-hydroxyester 5. The remaining functional groups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produce 2 in 34% overall yield from BOC-L-trans-4-hydroxyproline methylester 3 (Scheme 1). (C) 1997 Elsevier Science Ltd.

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页码：3203 / 3206

页数：4

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