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

Mostafa, M., McMillan, A. E. and Sutherland, A. (2017) Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates. Organic and Biomolecular Chemistry, 15(14), pp. 3035-3045. (doi: 10.1039/C7OB00456G) (PMID:28304410)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Mostafa, Mohamed and Sutherland, Dr Andrew
Authors: Mostafa, M., McMillan, A. E., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
Publisher:Royal Society of Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539
Published Online:14 March 2017
Copyright Holders:Copyright © 2017 The Authors
First Published:First published in Organic and Biomolecular Chemistry 15(14): 3035-3045
Publisher Policy:Reproduced under a Creative Commons License

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