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Synthesis of deoxyelephantopin analogues.

Authors
  • Lagoutte, Roman1
  • Serba, Christelle1
  • Winssinger, Nicolas1
  • 1 Faculty of Science, Department of Organic Chemistry, NCCR Chemical Biology, University of Geneva, Geneva, Switzerland. , (Switzerland)
Type
Published Article
Journal
The Journal of antibiotics
Publication Date
Feb 01, 2018
Volume
71
Issue
2
Pages
248–256
Identifiers
DOI: 10.1038/ja.2017.132
PMID: 29089602
Source
Medline
License
Unknown

Abstract

Deoxyelephantopin is a sesquiterpene lactone that was reported to be as effective in the treatment of mammary tumours and lung metastasis as taxol based on a murine orthotopic cancer model. Its germacrene skeleton harbours three Michael acceptors that can potentially engage a target covalently. Its strained 10-membered ring is densely functionalised and represents an important synthetic challenge. We herein describe our studies towards deoxyelephantopins using a ring-closing metathesis approach and report some unexpected observations.

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