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Synlett 2017; 28(04): 467-470
DOI: 10.1055/s-0036-1588917
letter
© Georg Thieme Verlag Stuttgart · New York

An Unprecedented Octahydro-3H-oxeto[2,3,4-ij]isochromene Ring System Formed by a Trichloromethyl-Anion-Induced Reaction Cascade

Witali Schmidt
a   Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany   Email: stefan.schulz@tu-bs.de
,
Peter G. Jones
b   Institute of Inorganic and Analytical Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
,
Jennifer Herrmann
c   Department Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Campus E8.1, 66123 Saarbrücken, Germany
,
Rolf Müller
c   Department Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, Saarland University, Campus E8.1, 66123 Saarbrücken, Germany
,
Stefan Schulz*
a   Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany   Email: stefan.schulz@tu-bs.de
› Author Affiliations
Further Information

Publication History

Received: 19 September 2016

Accepted after revision: 02 November 2016

Publication Date:
18 November 2016 (online)

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Abstract

Sigillin A is a unique polychlorinated, insect repellent natural product, isolated recently from springtails. During the exploitation of an access to such compounds using a trichloromethyl-anion-induced epoxide opening as key step a new synthetic compound was found. A five-step cascade reaction leads to an oxeto[2,3,4-ij]isochromene compound, including a rare oxetane acetal as well as an trichloroenol ether group. Biological data on the antibacterial properties of this compound and sigillin A are reported as well.

Key words

sigillin - springtails - dichlorocarbene - chlorinated natural products - hydrobenzopyranone - dimethyldioxirane - oxetane acetal - trichloroenol ether

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588917.
  • Supporting Information
 

  • References and Notes

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