(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues

Autor: Armin de Meijere, Sergei I. Kozhushkov, Dmitrii S. Yufit, Christian Grosse, Marcel Kaiser, Vitaly A. Raev
Jazyk: angličtina
Rok vydání: 2014
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 2844-2857 (2014)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.10.302
Popis: Efficient and scalable syntheses of enantiomerically pure (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-mono(di,tri)fluoromethylcyclopropyl]alanines 9a–c, as well as allo-D-threonine (4) and (2S,3R)-β-methylphenylalanine (3), using the Belokon' approach with (S)- and (R)-2-[(N-benzylprolyl)amino]benzophenone [(S)- and (R)-10] as reusable chiral auxiliaries have been developed. Three new fluoromethyl analogues of the naturally occurring octadepsipeptide hormaomycin (1) with (fluoromethylcyclopropyl)alanine moieties have been synthesized and subjected to preliminary tests of their antibiotic activity.
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