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

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-benzylp...

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Autores principales: de Meijere, Armin, Kozhushkov, Sergei I, Yufit, Dmitrii S, Grosse, Christian, Kaiser, Marcel, Raev, Vitaly A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273223/
https://www.ncbi.nlm.nih.gov/pubmed/25550751
http://dx.doi.org/10.3762/bjoc.10.302
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author de Meijere, Armin
Kozhushkov, Sergei I
Yufit, Dmitrii S
Grosse, Christian
Kaiser, Marcel
Raev, Vitaly A
author_facet de Meijere, Armin
Kozhushkov, Sergei I
Yufit, Dmitrii S
Grosse, Christian
Kaiser, Marcel
Raev, Vitaly A
author_sort de Meijere, Armin
collection PubMed
description 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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spelling pubmed-42732232014-12-30 (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues de Meijere, Armin Kozhushkov, Sergei I Yufit, Dmitrii S Grosse, Christian Kaiser, Marcel Raev, Vitaly A Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2014-12-03 /pmc/articles/PMC4273223/ /pubmed/25550751 http://dx.doi.org/10.3762/bjoc.10.302 Text en Copyright © 2014, de Meijere et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
de Meijere, Armin
Kozhushkov, Sergei I
Yufit, Dmitrii S
Grosse, Christian
Kaiser, Marcel
Raev, Vitaly A
(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
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
title_full (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
title_fullStr (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
title_full_unstemmed (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
title_short (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
title_sort (2r,1's,2'r)- and (2s,1's,2'r)-3-[2-mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273223/
https://www.ncbi.nlm.nih.gov/pubmed/25550751
http://dx.doi.org/10.3762/bjoc.10.302
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