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A synthetic approach to morphine

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
Ellwood, Charles Walter

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: 04 Jul 2022 20:17

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Contributors

Author: Charles Walter Ellwood

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