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Total syntheses of justicidin B and retrojusticidin B using a tandem Horner-Emmons-Claisen condensation sequence

Total syntheses of justicidin B and retrojusticidin B using a tandem Horner-Emmons-Claisen condensation sequence
Total syntheses of justicidin B and retrojusticidin B using a tandem Horner-Emmons-Claisen condensation sequence
Short syntheses of justicidin B 1 and retrojusticidin B 4 are reported. The key feature is a new annulation reaction, involving a base induced union of ketoaldehyde 2 and phosphonate 3. that is used to construct the highly substituted naphthalene core.
natural products, annulation, lignans, horner-emmons, claisen condensationlignan lactones, 1-arylnaphthalene lignans, arylnaphthalene lignans, neolignans, 5-lipoxygenase, cyanohydrins, inhibitors, agents, entry, cells
0040-4039
6973-6975
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bradley, M.
078a34d6-96c4-4ce1-9aa1-454d9ee0030d
Castro, J. L.
2a394157-ea90-4236-97aa-e8f2b72c0a90
Flanagan, S. R.
6a60460e-2572-4441-8693-6b591c5121aa
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Bradley, M.
078a34d6-96c4-4ce1-9aa1-454d9ee0030d
Castro, J. L.
2a394157-ea90-4236-97aa-e8f2b72c0a90
Flanagan, S. R.
6a60460e-2572-4441-8693-6b591c5121aa

Harrowven, D. C., Bradley, M., Castro, J. L. and Flanagan, S. R. (2001) Total syntheses of justicidin B and retrojusticidin B using a tandem Horner-Emmons-Claisen condensation sequence. Tetrahedron Letters, 42 (39), 6973-6975. (doi:10.1016/S0040-4039(01)01436-8).

Record type: Article

Abstract

Short syntheses of justicidin B 1 and retrojusticidin B 4 are reported. The key feature is a new annulation reaction, involving a base induced union of ketoaldehyde 2 and phosphonate 3. that is used to construct the highly substituted naphthalene core.

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More information

Published date: 24 September 2001
Keywords: natural products, annulation, lignans, horner-emmons, claisen condensationlignan lactones, 1-arylnaphthalene lignans, arylnaphthalene lignans, neolignans, 5-lipoxygenase, cyanohydrins, inhibitors, agents, entry, cells

Identifiers

Local EPrints ID: 19502
URI: http://eprints.soton.ac.uk/id/eprint/19502
ISSN: 0040-4039
PURE UUID: 4bb292f9-7435-412f-98b7-a338a65c2582
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 14 Feb 2006
Last modified: 20 Jul 2019 01:19

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