Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters

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Abstract

Dysoxylactam A is a 17-membered macrocyclic lipid which has been found to dramatically reverse multidrug resistance in cancer cells. Three previous syntheses have been reported in 15-17 steps. Using iterative lithiation-borylation reactions as the key C−C bond forming and stereocontrolling steps, we now describe an 11-step synthesis of dysoxylactam A. The complete sequence only required a total of five chromatographic purifications and used minimal protecting groups making it both rapid and efficient.
Original languageEnglish
Pages (from-to)2338-2341
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume10
Issue number9
Early online date10 Aug 2021
DOIs
Publication statusPublished - Sept 2021

Bibliographical note

Funding Information:
J.R thanks the Bristol Chemical Synthesis Centre for Doctoral Training and the EPSRC (EP/G036764/1) for funding, and the University of Bristol for a PhD studentship.

Publisher Copyright:
© 2021 The Authors. Asian Journal of Organic Chemistry published by Wiley-VCH GmbH

Structured keywords

  • BCS and TECS CDTs

Keywords

  • assembly-line
  • homologation
  • lithiation-borylation
  • macrocyclic synthesis
  • polyketides

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