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
收藏
页码：3295 / 3298
页数：4
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