Publication Date:
2014-12-04
Description:
Efficient and scalable syntheses of enantiomerically pure (2 R ,1' S ,2' R )- and (2 S ,1' S ,2' R )-3-[2-mono(di,tri)fluoromethylcyclopropyl]alanines 9a – c , as well as allo -D-threonine ( 4 ) and (2 S ,3 R )-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 J. Org. Chem. 2014, 10, 2844–2857. doi:10.3762/bjoc.10.302
Keywords:
amino acidsbiosynthesisbuilding blockscyclopropanesnatural productssynthetic methods
Electronic ISSN:
1860-5397
Topics:
Chemistry and Pharmacology
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