A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans


Flanagan, S. R., Harrowven, D. C. and Bradley, M. (2002) A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans. Tetrahedron, 58, (30), 5989-6001. (doi:10.1016/S0040-4020(02)00616-6).

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Description/Abstract

A new aromatic annulation reaction based on sequential Horner-Emmons and Claisen condensation reactions is described. The method is high yielding and provides a rapid entry to arylnaphthalenes. The lignan natural products justicidin B 1, retrojusticidin B 2, taiwanin C 3, justicidin E 4, chinensin 5 and retrochinensin 6 have all been synthesised in good overall yield using this protocol, demonstrating its potential in multiple parallel synthesis. The selective oxidation of diols 34-36 to the corresponding retrolactones with barium manganate(VI) is also noteworthy.

Item Type: Article
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Keywords: annulation, claisen condensation, combinatorial chemistry, homer-emmons, lignans, natural productsdiels-alder reaction, intramolecular cannizzaro reaction, modifyingantirheumatic drugs, 1-arylnaphthalene lignans, antiviral activity, reaction sequence, cascade process, justicidin-b, taiwanin-c, lactones
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19735
Date Deposited: 17 Feb 2006
Last Modified: 27 Mar 2014 18:09
URI: http://eprints.soton.ac.uk/id/eprint/19735

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