A synthetic approach to morphine
A synthetic approach to morphine
The synthesis of a putative intramolecular Diels-Alder reaction substrate, an intermediate in a synthetic approach to morphine, is described. The condensation reactions of several ortho-bromophenols with allylic bromides are described. The ortho-bromophenyl allyl ethers thus produced were treated with a catalytic quantity of palladium acetate to give a series of benzofuran derivatives. Several 3,4,7-trisubstituted benzofurans were produced. Two ortho-bromophenyl allyl ethers were subjected to radical cyclisation conditions. Two novel tetracyclic compounds were produced. The condensation of nitromethane with several aromatic aldehydes is described. The β-nitroethenyl-aromatic compounds produced were reduced to give the corresponding β-nitroethyl-aromatic compounds. The cycloaddition reactions of nitrones and silylnitronates to methyl E-2,4-pentadienoate are described. The isoxazole derivatives produced in these reactions were converted to dienyl or trienyl systems. The putative intramolecular Diels-Alder reaction substrate was produced using this methodology.
University of Southampton
Ellwood, Charles Walter
3a61d941-2523-4aaf-8f4b-3a0fb1096221
1989
Ellwood, Charles Walter
3a61d941-2523-4aaf-8f4b-3a0fb1096221
Ellwood, Charles Walter
(1989)
A synthetic approach to morphine.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The synthesis of a putative intramolecular Diels-Alder reaction substrate, an intermediate in a synthetic approach to morphine, is described. The condensation reactions of several ortho-bromophenols with allylic bromides are described. The ortho-bromophenyl allyl ethers thus produced were treated with a catalytic quantity of palladium acetate to give a series of benzofuran derivatives. Several 3,4,7-trisubstituted benzofurans were produced. Two ortho-bromophenyl allyl ethers were subjected to radical cyclisation conditions. Two novel tetracyclic compounds were produced. The condensation of nitromethane with several aromatic aldehydes is described. The β-nitroethenyl-aromatic compounds produced were reduced to give the corresponding β-nitroethyl-aromatic compounds. The cycloaddition reactions of nitrones and silylnitronates to methyl E-2,4-pentadienoate are described. The isoxazole derivatives produced in these reactions were converted to dienyl or trienyl systems. The putative intramolecular Diels-Alder reaction substrate was produced using this methodology.
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Published date: 1989
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Local EPrints ID: 461613
URI: http://eprints.soton.ac.uk/id/eprint/461613
PURE UUID: 49f75c85-0774-4146-baab-549e0104179a
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Date deposited: 04 Jul 2022 18:51
Last modified: 16 Mar 2024 18:49
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Author:
Charles Walter Ellwood
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