Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis

Marina Harras, Wolfgang Milius, R Alan Aitken*, Rainer Schobert*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)579-587
Number of pages9
JournalThe Journal of Organic Chemistry
Volume82
Issue number1
Early online date14 Dec 2016
DOIs
Publication statusPublished - 6 Jan 2017

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