Diastereoselective reaction of a Grignard reagent with chiral imides: A practical preparation of a key intermediate in the synthesis of ifetroban sodium

被引：17

作者：

Mueller, RH ^{[1
]}

Wang, SP ^{[1
]}

Pansegrau, PD ^{[1
]}

Jannotti, JQ ^{[1
]}

Poss, MA ^{[1
]}

Thottathil, JK ^{[1
]}

Singh, J ^{[1
]}

Humora, MJ ^{[1
]}

Kissick, TP ^{[1
]}

Boyhan, B ^{[1
]}

机构：

[1] Bristol Myers Squibb Pharmaceut Res Inst, Chem Proc Res Dept, Princeton, NJ 08543 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 1997年 / 1卷 / 01期

关键词：

D O I：

10.1021/op960034k

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel and highly efficient synthesis of [1S-(1 alpha,2 alpha,3 alpha,4 alpha)]-2-[[2-(3-methoxy-3-oxopropyl)phenyl]methyl]-7-oxabicyclo[2.2.1]-heptane-3-carboxylic acid (A), a key intermediate in the synthesis of ifetroban sodium, BMS-180291, is described. Reaction of chiral imides such as [2(S),3a alpha,4 beta,7 beta,7a alpha]-hexahydro-2-(1-phenylethyl)-4,7-epoxy-1H-isoindole-1,3(2H)-dione (B) with the Grignard reagent derived from 2-(2-bromophenyl)-1,3-dioxolane and subsequent in situ transformations give [2S-(2 alpha,3a alpha,4 beta,7 beta,7a alpha)]-2-(octahydro-3-oxo-4,7-epoxyisobenzofuran-1-yl)benzaldehyde, converted in two steps to A. Efficient syntheses of B from furan and maleic anhydride are described.

引用

页码：14 / 19

页数：6

共 12 条

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