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

A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans
A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans
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.
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
0040-4020
5989-6001
Flanagan, S. R.
6a60460e-2572-4441-8693-6b591c5121aa
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bradley, M.
078a34d6-96c4-4ce1-9aa1-454d9ee0030d
Flanagan, S. R.
6a60460e-2572-4441-8693-6b591c5121aa
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bradley, M.
078a34d6-96c4-4ce1-9aa1-454d9ee0030d

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).

Record type: Article

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.

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More information

Published date: 22 July 2002
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

Identifiers

Local EPrints ID: 19735
URI: http://eprints.soton.ac.uk/id/eprint/19735
ISSN: 0040-4020
PURE UUID: e388822f-a283-4f59-928c-3dbecb3eedc6
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 09 Jan 2022 02:46

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Contributors

Author: S. R. Flanagan
Author: D. C. Harrowven ORCID iD
Author: M. Bradley

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