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
Number of pages5
JournalAsian Journal of Organic Chemistry
Early online date10 Aug 2021
DOIs
Publication statusE-pub ahead of print - 10 Aug 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

Keywords

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

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