Abstract:
All the four stereoisomers of 3-(trans-2-aminocyclopropyl)alanine – a key constituent of the potential antitumor agent belactosin A – were prepared by simple catalytic hydrogenation of (2S,1'S,2'S)-, (2S,1’R,2’R)-, (2R,1’R,2’R)-, and (2R,1'S,2'S)-3-(trans-2-nitrocyclopropyl) alanines in 95, 93, 91 and 92% yields, respectively.
Document Type:
Article
Language: English
Citation:
O. V. Larionov, S. I. Kozhushkov, M. Brandl, A. de Meijere, “Rational synthesis of all the four stereoisomers of 3-(trans-2-aminocyclopropyl)alanine”, Mendeleev Commun., 13:5 (2003), 199–200
Linking options:
https://www.mathnet.ru/eng/mendc4021
https://www.mathnet.ru/eng/mendc/v13/i5/p199
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N. V. Yashin, N. E. Tikhomirova, K. N. Sedenkova, D. A. Vasilenko, Yu. K. Grishin, T. S. Kuznetsova, E. B. Averina, “Novel synthetic approach to non-natural conformationally rigid spiro-linked amino acids”, Russ Chem Bull, 68:3 (2019), 547
Valentin A. Rassadin, Yvan Six, “Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives”, Tetrahedron, 72:32 (2016), 4701
Sébastien F. Vanier, Guillaume Larouche, Ryan P. Wurz, André B. Charette, “Formal Synthesis of Belactosin A and Hormaomycin via a Diastereoselective Intramolecular Cyclopropanation of an α-Nitro Diazoester”, Org. Lett., 12:4 (2010), 672
Farina Brackmann, Armin de Meijere, “Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 2. 3,4- and 4,5-Methanoamino Acids”, Chem. Rev., 107:11 (2007), 4538
Sung Wook Cho, Daniel Romo, “Total Synthesis of (-)-Belactosin C and Derivatives via Double Diastereoselective Tandem Mukaiyama Aldol Lactonizations”, Org. Lett., 9:8 (2007), 1537
Boris D. Zlatopolskiy, Markus Radzom, Axel Zeeck, Armin de Meijere, “Synthesis and Precursor‐Directed Biosynthesis of New Hormaomycin Analogues”, Eur J Org Chem, 2006:6 (2006), 1525
Sergei I. Kozhushkov, Boris D. Zlatopolskiy, Melanie Brandl, Petra Alvermann, Markus Radzom, Bernardette Geers, Armin de Meijere, Axel Zeeck, “Hormaomycin Analogues by Precursor‐Directed Biosynthesis – Synthesis of and Feeding Experiments with Amino Acids Related to the Unique 3‐(trans‐2‐Nitrocyclopropyl)alanine Constituent”, Eur J Org Chem, 2005:5 (2005), 854
Melanie Brandl, Sergei I. Kozhushkov, Boris D. Zlatopolskiy, Petra Alvermann, Bernadette Geers, Axel Zeeck, Armin de Meijere, “The Biosynthesis of 3‐(trans‐2‐Nitrocyclopropyl)alanine, a Constituent of the Signal Metabolite Hormaomycin”, Eur J Org Chem, 2005:1 (2005), 123
Alan Armstrong, James N. Scutt, “Total synthesis of (+)-belactosin A”, Chem. Commun., 2004, no. 5, 510
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