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17 Nov 23:00

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

by Schmidt, Witali

Synlett
DOI: 10.1055/s-0036-1588917



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.
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