title: (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues.
abstract: 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.
authors.affiliation: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.
authors.forename: Armin
authors.initials: A
authors.lastname: de Meijere
authors.affiliation: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.
authors.forename: Sergei I
authors.initials: SI
authors.lastname: Kozhushkov
authors.affiliation: Department of Chemistry, University of Durham, South Rd., Durham DH1 3L, UK.
authors.forename: Dmitrii S
authors.initials: DS
authors.lastname: Yufit
authors.affiliation: Institut für Anorganische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Grosse
authors.affiliation: Swiss Tropical and Public Health Institute, Parasite Chemotherapy, Socinstrasse 57, CH-4002 Basel, Switzerland ; University of Basel, Petersplatz, 1 CH-4003 Basel Switzerland.
authors.forename: Marcel
authors.initials: M
authors.lastname: Kaiser
authors.affiliation: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany ; Institut für Organische Chemie der TU Carolo-Wilhelmina zu Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Vitaly A
authors.initials: VA
authors.lastname: Raev
keywords: amino acids; biosynthesis; building blocks; cyclopropanes; natural products; synthetic methods