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Issue 14, 2017
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Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates

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Abstract

The amino substituted bicyclo[4.3.0]nonane is a molecular scaffold found in a wide range of natural products and medicinal agents. Despite this, synthetic methods for the general preparation of this structural motif are sparse. Here we evaluate a diastereoselective approach for the preparation of vinylsilyl derived aminobicyclo[4.3.0]nonanes using a one-pot multi-bond forming process involving a Pd(II)-catalysed Overman rearrangement, a Ru(II)-catalysed ring closing enyne metathesis reaction, followed by a hydrogen bonding directed Diels–Alder reaction. We show that a benzyldimethylsilyl-substituted alkene analogue is amenable to further functionalisation and the late stage generation of diverse sp3-rich, drug-like aminobicyclo[4.3.0]nonane scaffolds with up to six stereogenic centres.

Graphical abstract: Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates

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Publication details

The article was received on 23 Feb 2017, accepted on 13 Mar 2017 and first published on 14 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00456G
Citation: Org. Biomol. Chem., 2017,15, 3035-3045
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    Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates

    M. A. B. Mostafa, A. E. McMillan and A. Sutherland, Org. Biomol. Chem., 2017, 15, 3035
    DOI: 10.1039/C7OB00456G

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