通过二酰基过氧化物的光解合成β-环丙基丙氨酸。

Synthesis of beta-cyclopropylalanines by photolysis of diacyl peroxides.

作者信息

Jain Rajendra P, Vederas John C

机构信息

Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.

出版信息

Org Lett. 2003 Nov 27;5(24):4669-72. doi: 10.1021/ol035859a.

DOI:10.1021/ol035859a

PMID:14627411

Abstract

[reaction: see text] Photolysis at 254 nm of neat (no solvent) unsymmetrical diacyl peroxides derived from cyclopropane carboxylic acids and l-aspartic acid generates protected beta-cyclopropylalanines in reasonable yields. Orthogonally protected 3-(trans-2-aminocyclopropyl)alanine (21), a key constituent of the antitumor agent belactosin A, as well as protected hypoglycin A (26), a causative agent of Jamaican vomiting sickness, is synthesized by this approach with coupling of the intermediate substituted cyclopropyl radicals proceeding predominantly with retention of configuration (dr >or= 95:5).

摘要

[反应：见正文] 由环丙烷羧酸和L-天冬氨酸衍生的纯（无溶剂）不对称二酰基过氧化物在254 nm光解，以合理的产率生成受保护的β-环丙基丙氨酸。通过这种方法合成了抗肿瘤剂贝拉缩菌素A的关键成分正交保护的3-(反式-2-氨基环丙基)丙氨酸(21)以及牙买加呕吐病病原体受保护的降糖氨酸A(26)，中间体取代环丙基自由基的偶联主要以构型保持进行（dr≥95:5）。