An asymmetric synthesis of aza analogues of the tricyclic skeleton of daphnane and the ABC ring system of phorbol
An asymmetric synthesis of aza analogues of the tricyclic skeleton of daphnane and the ABC ring system of phorbol
An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.
protein kinase-c, hypervalent iodine oxidation, ester pharmacophore, tumor promoters, malic-acid, (+)-heliotridine, cyclizations, convergent, annulation, reduction
792-798
Marson, Charles M.
28f9225a-51fa-4c2b-848c-b77b225f53cb
Pink, Jennifer H.
73884d13-9316-4e1f-a190-4a352cb5c9c2
Hall, David
5cf4eeb4-5247-4663-bc36-f7792a6c2c04
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Malik, Abdul
8bdd99bd-29ce-4c1e-be29-7ebdf65c7ebe
Smith, Christopher
969cad82-7677-470b-8997-c9a8c3cb0e13
7 February 2003
Marson, Charles M.
28f9225a-51fa-4c2b-848c-b77b225f53cb
Pink, Jennifer H.
73884d13-9316-4e1f-a190-4a352cb5c9c2
Hall, David
5cf4eeb4-5247-4663-bc36-f7792a6c2c04
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Malik, Abdul
8bdd99bd-29ce-4c1e-be29-7ebdf65c7ebe
Smith, Christopher
969cad82-7677-470b-8997-c9a8c3cb0e13
Marson, Charles M., Pink, Jennifer H., Hall, David, Hursthouse, Michael B., Malik, Abdul and Smith, Christopher
(2003)
An asymmetric synthesis of aza analogues of the tricyclic skeleton of daphnane and the ABC ring system of phorbol.
Journal of Organic Chemistry, 68 (3), .
(doi:10.1021/jo0205816).
Abstract
An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.
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Published date: 7 February 2003
Keywords:
protein kinase-c, hypervalent iodine oxidation, ester pharmacophore, tumor promoters, malic-acid, (+)-heliotridine, cyclizations, convergent, annulation, reduction
Identifiers
Local EPrints ID: 20040
URI: http://eprints.soton.ac.uk/id/eprint/20040
ISSN: 0022-3263
PURE UUID: cebdea88-5017-4e98-8335-0bd7a9ec2883
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Date deposited: 24 Feb 2006
Last modified: 15 Mar 2024 06:21
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Contributors
Author:
Charles M. Marson
Author:
Jennifer H. Pink
Author:
David Hall
Author:
Abdul Malik
Author:
Christopher Smith
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