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Issue 21, 2018
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Synthesis of fused tricyclic systems by thermal Cope rearrangement of furan-substituted vinyl cyclopropanes

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Abstract

A novel method for the stereoselective construction of hexahydroazuleno[4,5-b]furans from simple precursors has been developed. The route involves the use of our recently developed Brønsted acid catalysed cyclisation reaction of acyclic ynenones to prepare fused 1-furanyl-2-alkenylcyclopropanes that undergo highly stereoselective thermal Cope rearrangement to produce fused tricyclic products. Substrates possessing an E-alkene undergo smooth Cope rearrangement at 40 °C, whereas the corresponding Z-isomers do not react at this temperature. Computational studies have been performed to explain the difference in behaviour of the E- and Z-isomers in the Cope rearrangement reaction. The hexahydroazuleno[4,5-b]furans produced by Cope rearrangement have potential as advanced intermediates for the synthesis of members of the guaianolide family of natural products.

Graphical abstract: Synthesis of fused tricyclic systems by thermal Cope rearrangement of furan-substituted vinyl cyclopropanes

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Publication details

The article was received on 19 Apr 2018, accepted on 04 May 2018 and first published on 15 May 2018


Article type: Paper
DOI: 10.1039/C8OB00924D
Citation: Org. Biomol. Chem., 2018,16, 3970-3982
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    Synthesis of fused tricyclic systems by thermal Cope rearrangement of furan-substituted vinyl cyclopropanes

    V. Klaus, S. Wittmann, H. M. Senn and J. S. Clark, Org. Biomol. Chem., 2018, 16, 3970
    DOI: 10.1039/C8OB00924D

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