(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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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.10.302 |
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doaj-d98067659fc24c0a80319c6d1efd5c992021-04-02T15:32:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-12-011012844285710.3762/bjoc.10.3021860-5397-10-302(2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analoguesArmin de Meijere0Sergei I. Kozhushkov1Dmitrii S. Yufit2Christian Grosse3Marcel Kaiser4Vitaly A. Raev5Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanyInstitut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanyDepartment of Chemistry, University of Durham, South Rd., Durham DH1 3L, UKInstitut für Anorganische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, GermanySwiss Tropical and Public Health Institute, Parasite Chemotherapy, Socinstrasse 57, CH-4002 Basel, SwitzerlandInstitut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanyEfficient 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.https://doi.org/10.3762/bjoc.10.302amino acidsbiosynthesisbuilding blockscyclopropanesnatural productssynthetic methods |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Armin de Meijere Sergei I. Kozhushkov Dmitrii S. Yufit Christian Grosse Marcel Kaiser Vitaly A. Raev |
| spellingShingle |
Armin de Meijere Sergei I. Kozhushkov Dmitrii S. Yufit Christian Grosse Marcel Kaiser Vitaly A. Raev (2R,1'S,2'R)- and (2S,1'S,2'R)-3-[2-Mono(di,tri)fluoromethylcyclopropyl]alanines and their incorporation into hormaomycin analogues Beilstein Journal of Organic Chemistry amino acids biosynthesis building blocks cyclopropanes natural products synthetic methods |
| author_facet |
Armin de Meijere Sergei I. Kozhushkov Dmitrii S. Yufit Christian Grosse Marcel Kaiser Vitaly A. Raev |
| author_sort |
Armin de Meijere |
| 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_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_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_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 |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2014-12-01 |
| 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. |
| topic |
amino acids biosynthesis building blocks cyclopropanes natural products synthetic methods |
| url |
https://doi.org/10.3762/bjoc.10.302 |
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