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 |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Mostafa, Mohamed and Sutherland, Professor 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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