title: Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates.
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.
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Mohamed A B
authors.initials: MA
authors.lastname: Mostafa
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Angus E
authors.identifier: http://orcid.org/0000-0002-8883-1380
authors.initials: AE
authors.lastname: McMillan
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Andrew
authors.identifier: http://orcid.org/0000-0001-7907-5766
authors.initials: A
authors.lastname: Sutherland