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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| Related URLs: | |
| 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 |
| Item ID: | 19735 |
| Date Deposited: | 17 Feb 2006 |
| Last Modified: | 01 Jun 2011 16:10 |
| Contributors: | Flanagan, S. R. (Author) Harrowven, D. C. (Author) Bradley, M. (Author) |
| Date: | 22 July 2002 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19735 |
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