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Synlett 2000; 2000(12): 1741-1744
DOI: 10.1055/s-2000-8679
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Synthesis of trans-(2-Aminocyclopropyl)alanine - A Key Constituent of the Novel Antitumor Antibiotic Belactosin A

Melanie Brandl* , Sergei I. Kozhushkov, Karin Loscha, Olga V. Kokoreva, Dimitrii S. Yufit, Judith A. K. Howard, Armin de Meijere
  • *Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany; E-mail: Armin-deMeijere@chemie.uni-goettingen.de
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Publication Date:
31 December 2000 (online)

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Racemic 3-(trans-2-aminocyclopropyl)alanine was prepared in its 3,3-dideuterio-labelled form 3b from tert-butyl 2,3-dibromopropanoate 4 and nitromethane through a nine-step sequence in 8% overall yield. The newly developed access to enantiomerically pure (trans-2-nitrocyclopropyl)methanol (S,S)-6a also constitutes a formal synthesis of enantiomerically pure 3-(trans-2-aminocyclopropyl)alanine (S,S,S)-3a, a key intermediate for the total synthesis of the novel antitumor antibiotic belactosin A.

amino acids - amino alcohols - antitumor agents - cyclopropanes - enantiomeric resolution