Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and derivatives

被引：29

作者：

Cheng, WC

Liu, YN

Wong, M

Olmstead, MM

Lam, KS

Kurth, MJ

机构：

[1] Univ Calif Davis, Davis, CA 95616 USA

[2] Univ Calif Davis, Ctr Canc, Dept Internal Med, Div Hematol & Oncol, Sacramento, CA 95817 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 16期

关键词：

D O I：

10.1021/jo025611j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exo-methyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereo-selectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisox-azolinoproline amino acids.

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页码：5673 / 5677

页数：5

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