Synthesis of beta-cyclopropylalanines by photolysis of diacyl peroxides.
[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).
Jain
Rajendra P
RP
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Vederas
John C
JC
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007005:Hypoglycins / Q000138:chemical synthesis / Q000737:chemistry; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides / Q000737:chemistry; D010545:Peroxides / Q000737:chemistry*; D010782:Photolysis
D007005:Hypoglycins; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; D010545:Peroxides; C406052:belactosin A; C041757:hypoglycin; D000409:Alanine