Synthesis of the Active Form of Loxoprofen by Using Allylic Substitutions in Two Steps

被引：28

作者：

Hyodo, Tomonori ^{[1
]}

Kiyotsuka, Yohei ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 05期

关键词：

EFFICIENT SYNTHESIS; RESOLUTION; REAGENTS; COPPER; ARYL;

D O I：

10.1021/ol802949c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High regioselectivity for allylic substitution of the cyclopentenyl picolinate 5 with benzylcopper reagent was attained with ZnBr2, and the finding was applied to the p-BrC6H4CH2 reagent. The cyclopentene moiety In the product was reduced to the cyclopentane, and the P-BrC6H4 was converted to the "Cu"C6H4 for the second allylic substitution with picolinate 8 to furnish the title compound after oxidative cleavage of the resulting olefin moiety.

引用

页码：1103 / 1106

页数：4

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