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

4 Citations (Scopus)

46 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

Structured keywords

BrisSynBio
Bristol BioDesign Institute
BCS and TECS CDTs

Access to Document

10.1021/acs.orglett.0c02190

Full-text PDF (author’s accepted manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at https://pubs.acs.org/doi/10.1021/acs.orglett.0c02190 . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 716 KB

Handle.net

Persistent link

Cite this

@article{dbe2853b18a64449872a0b98d6210875,

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.",

author = "Davies, {Jonathan A} and Bull, {Freya M} and Walker, {Paul D} and Weir, {Angus N M} and Rob Lavigne and Joleen Masschelein and Simpson, {Thomas J} and Race, {Paul R} and Crump, {Matthew P} and Willis, {Christine L}",

year = "2020",

month = aug,

day = "21",

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

language = "English",

volume = "22",

pages = "6349--6353",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

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.

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

Structured keywords

Access to Document

Handle.net

Fingerprint

Cite this