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

doi:10.1021/acs.joc.6b02586

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 journal › Article › peer-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 language	English
Pages (from-to)	579-587
Number of pages	9
Journal	The Journal of Organic Chemistry
Volume	82
Issue number	1
Early online date	14 Dec 2016
DOIs	https://doi.org/10.1021/acs.joc.6b02586
Publication status	Published - 6 Jan 2017

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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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title = "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.",

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T1 - Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis

AU - Harras, Marina

AU - Milius, Wolfgang

AU - Aitken, R Alan

AU - Schobert, Rainer

PY - 2017/1/6

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N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85018462191

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DO - 10.1021/acs.joc.6b02586

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JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 1

ER -

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

Abstract

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