Studies towards the synthesis of the active constituents of feverfew
Studies towards the synthesis of the active constituents of feverfew
A route to the guaianolide sesquiterpenes via a tandem radical cyclization has been studied. In a model study, a suitably substituted alkenyl bromide underwent 5-exo-trig cyclization forming the expected α-methylene-γ-butyrolactone ring. An efficient conjugate addition enolate trapping sequence on 2-cyclopentenone provided the basis for continuation of this methodology. Tandem radical cyclization of the elaborated starting material gave inconclusive results. Investigations were also carried out upon the germacranolide sesquiterpenes, involving the conjugate addition of an isocyanide to an α-ketoallene. The route revealed an interesting cyclization and hydration sequence of 8-substituted 4-ketoallenes.
University of Southampton
Henshilwood, James Andrew
1989
Henshilwood, James Andrew
Henshilwood, James Andrew
(1989)
Studies towards the synthesis of the active constituents of feverfew.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A route to the guaianolide sesquiterpenes via a tandem radical cyclization has been studied. In a model study, a suitably substituted alkenyl bromide underwent 5-exo-trig cyclization forming the expected α-methylene-γ-butyrolactone ring. An efficient conjugate addition enolate trapping sequence on 2-cyclopentenone provided the basis for continuation of this methodology. Tandem radical cyclization of the elaborated starting material gave inconclusive results. Investigations were also carried out upon the germacranolide sesquiterpenes, involving the conjugate addition of an isocyanide to an α-ketoallene. The route revealed an interesting cyclization and hydration sequence of 8-substituted 4-ketoallenes.
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Published date: 1989
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Local EPrints ID: 461726
URI: http://eprints.soton.ac.uk/id/eprint/461726
PURE UUID: e8b09cf3-2ae1-46bc-8ff5-42f2bfbaaae2
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Date deposited: 04 Jul 2022 18:52
Last modified: 04 Jul 2022 18:52
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Author:
James Andrew Henshilwood
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