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
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
24 September 2001
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), .
(doi:10.1016/S0040-4039(01)01436-8).
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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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
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Date deposited: 14 Feb 2006
Last modified: 16 Mar 2024 02:46
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Contributors
Author:
M. Bradley
Author:
J. L. Castro
Author:
S. R. Flanagan
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