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01770 am a22002413u 4500 |
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103978 |
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|a Speed, Alexander W. H.
|e author
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|a Massachusetts Institute of Technology. Department of Chemistry
|e contributor
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|a Schrock, Richard Royce
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|a Mann, Tyler J.
|e author
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|a O'Brien, Robert V.
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|a Schrock, Richard Royce
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|a Hoveyda, Amir H.
|e author
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|a Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C[subscript 1]
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|a Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C1
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|b American Chemical Society (ACS),
|c 2016-08-25T16:02:08Z.
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|z Get fulltext
|u http://hdl.handle.net/1721.1/103978
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|a 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.
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|a National Institutes of Health (U.S.) (NIH (GM-59426)
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|a en_US
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|a Article
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|t Journal of the American Chemical Society
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