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.
Bibliographical noteFunding 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.
© 2021 The Authors. Asian Journal of Organic Chemistry published by Wiley-VCH GmbH
- macrocyclic synthesis