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 language | English |
|---|---|
| Pages (from-to) | 2338-2341 |
| Number of pages | 4 |
| Journal | Asian Journal of Organic Chemistry |
| Volume | 10 |
| Issue number | 9 |
| Early online date | 10 Aug 2021 |
| DOIs | |
| Publication status | Published - 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
Research Groups and Themes
- BCS and TECS CDTs
Keywords
- assembly-line
- homologation
- lithiation-borylation
- macrocyclic synthesis
- polyketides
Access to Document
- Full-text PDF (final published version)
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