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Total Synthesis of the Tubulin Inhibitor WF-1360F Based on Macrocycle Formation through Ring-Closing Alkyne Metathesis


  • 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.


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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).

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