Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation

被引：38

作者：

Andrus, Merritt B. ^{[1
]}

Hicken, Erik J. ^{[1
]}

Stephens, Jeffrey C. ^{[1
]}

Bedke, D. Karl ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 22期

关键词：

PROTEIN FARNESYLTRANSFERASE INHIBITORS; ALPHA-AMINO-ACIDS; PAECILOMYCES SP FO-3684; STEREOSELECTIVE-SYNTHESIS; TRANSFER CATALYSTS; ENANTIOSELECTIVE SYNTHESIS; GLYCOLATE ALKYLATION; DERIVATIVES; METATHESIS; ALDEHYDES;

D O I：

10.1021/jo061395t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the farnesyltransferase inhibitor kurasoin A has been achieved using a novel asymmetric phase-transfer-catalyzed glycolate alkylation reaction. 2,5-Dimethoxyacetophenone 7 with cinchonidinium catalyst 9 (10 mol %) and hydroxide base with pivaloyl benzyl bromide 8 provided S-alkylation product 10 in high yield (80-99%) and excellent enantioselectivity. Baeyer-Villiger oxidation, Weinreb amide formation, and benzyl Grignard addition to the TES-ether 17 gave the protected target. Lithium hydroxide and peroxide generated kurasoin A ([alpha](D) + 8.4 degrees) without isomerization.

引用

页码：8651 / 8654

页数：4

共 35 条

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