A short enantioselective synthesis of N-boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid from geraniol

被引：6

作者：

Noe, Mark C. ^{[1
]}

Hawkins, Joel M. ^{[1
]}

Snow, Sheri L. ^{[1
]}

Wolf-Gouveia, Lilli ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Groton, CT 06340 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 08期

关键词：

D O I：

10.1021/jo800080t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.

引用

页码：3295 / 3298

页数：4

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