Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1]
Name
Schrock_Catalytic Z.pdf
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1.12 MB
Format
Adobe PDF
Checksum (MD5)
bdc76c7a8b2d2d40cae978eed9b49d64
Author(s)
Speed, Alexander W. H.
Mann, Tyler J.
O’Brien, Robert V.
Schrock, Richard Royce
Hoveyda, Amir H.
Alternative Title
Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C1
Date Issued
November 2014
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Speed, Alexander W. H., Tyler J. Mann, Robert V. O’Brien, Richard R. Schrock, and Amir H. Hoveyda. "Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1]. Journal of the American Chemical Society 136:46 (2014), pp 16136-16139. © 2014 American Chemical Society.
Version
Final published version
Abstract
A convergent diastereo- and enantioselective total synthesis of anticancer and antifungal macrocyclic natural product disorazole C1 is reported. The central feature of the successful route is the application of catalytic Z-selective cross-metathesis (CM). Specifically, we illustrate that catalyst-controlled stereoselective CM can be performed to afford structurally complex Z-alkenyl–B(pin) as well as Z-alkenyl iodide compounds reliably, efficiently, and with high selectivity (pin = pinacolato). The resulting intermediates are then joined in a single-step operation through catalytic inter- and intramolecular cross-coupling to furnish the desired 30-membered ring macrocycle containing the critical (Z,Z,E)-triene moieties.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja509973r
