Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis
Abstract
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.
Citation
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
Publication
The Journal of Organic Chemistry
Status
Peer reviewed
ISSN
0022-3263Type
Journal article
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