Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis
View/
Date
06/01/2017Metadata
Show full item recordAltmetrics Handle Statistics
Altmetrics DOI Statistics
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 ' , Journal of Organic Chemistry , vol. 82 , no. 1 , pp. 579-587 . https://doi.org/10.1021/acs.joc.6b02586
Publication
Journal of Organic Chemistry
Status
Peer reviewed
ISSN
0022-3263Type
Journal article
Rights
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
Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.