Total Synthesis of Kalimantacin A

Jonathan A 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

doi:10.1021/acs.orglett.0c02190

Total Synthesis of Kalimantacin A

Jonathan A 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

Research output: Contribution to journal › Article (Academic Journal) › peer-review

8 Citations (Scopus)

159 Downloads (Pure)

Abstract

The kalimantacins are a family of hybrid polyketide-nonribosomal peptide derived natural products that display potent and selective antibiotic activity against multi-drug 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 SAR studies and clinical evaluation.

Original language	English
Pages (from-to)	6349-6353
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	16
Early online date	10 Aug 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c02190
Publication status	Published - 21 Aug 2020

Research Groups and Themes

BrisSynBio
Bristol BioDesign Institute
BCS and TECS CDTs
Organic & Biological

Keywords

synthetic biology

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10.1021/acs.orglett.0c02190

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title = "Total Synthesis of Kalimantacin A",

abstract = "The kalimantacins are a family of hybrid polyketide-nonribosomal peptide derived natural products that display potent and selective antibiotic activity against multi-drug 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 SAR studies and clinical evaluation.",

keywords = "synthetic biology",

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year = "2020",

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doi = "10.1021/acs.orglett.0c02190",

language = "English",

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journal = "Organic Letters",

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TY - JOUR

T1 - Total Synthesis of Kalimantacin A

AU - Davies, Jonathan A

AU - Bull, Freya M

AU - Walker, Paul D

AU - Weir, Angus N M

AU - Lavigne, Rob

AU - Masschelein, Joleen

AU - Simpson, Thomas J

AU - Race, Paul R

AU - Crump, Matthew P

AU - Willis, Christine L

PY - 2020/8/21

Y1 - 2020/8/21

N2 - The kalimantacins are a family of hybrid polyketide-nonribosomal peptide derived natural products that display potent and selective antibiotic activity against multi-drug 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 SAR studies and clinical evaluation.

AB - The kalimantacins are a family of hybrid polyketide-nonribosomal peptide derived natural products that display potent and selective antibiotic activity against multi-drug 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 SAR studies and clinical evaluation.

KW - synthetic biology

U2 - 10.1021/acs.orglett.0c02190

DO - 10.1021/acs.orglett.0c02190

M3 - Article (Academic Journal)

C2 - 32806153

SN - 1523-7060

VL - 22

SP - 6349

EP - 6353

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Total Synthesis of Kalimantacin A

Abstract

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