These authors contributed equally to this work.
Total Synthesis of the Tubulin Inhibitor WF-1360F Based on Macrocycle Formation through Ring-Closing Alkyne Metathesis †
Article first published online: 22 APR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 22, pages 5866–5870, May 27, 2013
How to Cite
Neuhaus, C. M., Liniger, M., Stieger, M. and Altmann, K.-H. (2013), Total Synthesis of the Tubulin Inhibitor WF-1360F Based on Macrocycle Formation through Ring-Closing Alkyne Metathesis . Angew. Chem. Int. Ed., 52: 5866–5870. doi: 10.1002/anie.201300576
This work was supported by the Swiss National Science Foundation (SNF) (Project 200021_126511). We are very grateful to Prof. Dr. Alois Fürstner, MPI für Kohlenforschung, Mülheim (Germany), for the generous donation of samples of his catalysts.
- Issue published online: 17 MAY 2013
- Article first published online: 22 APR 2013
- Manuscript Received: 22 JAN 2013
- Swiss National Science Foundation (SNF). Grant Number: 200021_126511
- drug discovery;
- natural products;
- total synthesis
Key steps in this total synthesis of the antimitotic natural product WF-1360F (3) include the formation of the macrocycle through ring-closing alkyne metathesis and the subsequent conversion of the ensuing alkyne moiety into an E-configured double bond. As illustrated by the synthesis of 4, the macrocyclic vinyl iodide 2 can also serve as a common precursor for the synthesis of side-chain-modified rhizoxin analogues (see scheme; TIPS=triisopropylsilyl).