Synthesis of β-Cyclopropylalanines by Photolysis of Diacyl Peroxides
- 31 October 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (24), 4669-4672
- https://doi.org/10.1021/ol035859a
Abstract
Photolysis at 254 nm of neat (no solvent) unsymmetrical diacyl peroxides derived from cyclopropane carboxylic acids and l-aspartic acid generates protected β-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 ≥ 95:5).Keywords
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