Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis
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We report the syntheses of combretastatins D-2 and D-4 as well as a formal synthesis of combretastatin D-1 by a conceptually new route harnessing a ring-contracting flash vacuum pyrolytic extrusion of sulfur dioxide from the respective 16-membered sulfone precursors. Via flash vacuum pyrolysis, even metaparacyclophanes as small and strained as the hitherto unknown oxa[1.5]metaparacyclophane could be prepared as a side product en route to combretastatin D-2 by synchronous extrusion of SO2 and CO2.
Harras , M , Milius , W , Aitken , R A & Schobert , R 2017 , ' Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis ' , The Journal of Organic Chemistry , vol. 82 , no. 1 , pp. 579-587 . https://doi.org/10.1021/acs.joc.6b02586
The Journal of Organic Chemistry
Copyright © 2016 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1021/acs.joc.6b02586
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