Rapid structural diversification of pseudopterosins : sulfuric acid promoted dehydro-aromatization yielding 14,15-dihydro-elisabatin B

MCCULLOCH, Malcolm and KERR, Russell G. (2015). Rapid structural diversification of pseudopterosins : sulfuric acid promoted dehydro-aromatization yielding 14,15-dihydro-elisabatin B. Tetrahedron Letters, 56 (15), 2030-2033.

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2015.03.013
Link to published version:: 10.1016/j.tetlet.2015.03.013

Abstract

Herein, we report a one-pot, sulfuric acid promoted, dehydro-aromatization reaction to rapidly convert pseudopterosins into 14,15-dihydro-elisabatin B. We propose a mechanism invoking redox cycling between the substrate catechol and ortho-quinone moieties. We also provide full spectroscopic characterization of two novel 5,6-dihydro-1. H-phenalen-2(4. H)-one derivatives, which are minor products of the reaction. This work opens up a unique route to rapidly provide libraries of novel marine natural product derivatives for drug discovery.

Item Type: Article
Research Institute, Centre or Group: Biomolecular Sciences Research Centre
Identification Number: 10.1016/j.tetlet.2015.03.013
Depositing User: Hilary Ridgway
Date Deposited: 26 Mar 2015 10:31
Last Modified: 24 Apr 2015 13:50
URI: http://shura.shu.ac.uk/id/eprint/9575

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