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Synlett 2017; 28(04): 467-470
DOI: 10.1055/s-0036-1588917
DOI: 10.1055/s-0036-1588917
letter
An Unprecedented Octahydro-3H-oxeto[2,3,4-ij]isochromene Ring System Formed by a Trichloromethyl-Anion-Induced Reaction Cascade
Further Information
Publication History
Received: 19 September 2016
Accepted after revision: 02 November 2016
Publication Date:
18 November 2016 (online)
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 etherSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588917.
- Supporting Information
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References and Notes
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