Total Synthesis of Kalimantacin A | Zendy

J. Davies | Zendy; Freya M. Bull | Zendy; Paul D. Walker | Zendy; Angus N. M. Weir | Zendy; Rob Lavigne | Zendy; Joleen Masschelein | Zendy; Thomas J. Simpson | Zendy; Paul R. Race | Zendy; Matthew P. Crump | Zendy; Christine L. Willis | Zendy

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Total Synthesis of Kalimantacin A

Author(s) -

J. Davies,

Freya M. Bull,

Paul D. Walker,

Angus N. M. Weir,

Rob Lavigne,

Joleen Masschelein,

Thomas J. Simpson,

Paul R. Race,

Matthew P. Crump,

Christine L. Willis

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02190

Subject(s) - chemistry , total synthesis , sonogashira coupling , enantioselective synthesis , polyketide , combinatorial chemistry , stereochemistry , amide , staphylococcus aureus , nonribosomal peptide , peptide , bacteria , organic chemistry , biosynthesis , catalysis , biochemistry , palladium , biology , genetics , enzyme

The kalimantacins make up a family of hybrid polyketide-nonribosomal peptide-derived natural products that display potent and selective antibiotic activity against multidrug resistant strains of Staphylococcus aureus . Herein, we report the first total synthesis of kalimantacin A, in which three fragments are prepared and then united via Sonogashira and amide couplings. The enantioselective synthetic approach is convergent, unlocking routes to further kalimantacins and analogues for structure-activity relationship studies and clinical evaluation.

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