Cycloadditions in the synthesis of biologically active natural products
Cycloadditions in the synthesis of biologically active natural products
The preparation and reactivity of β-lactones is discussed and is followed by a review of the biological activity, structure and synthesis of the natural β-lactones. The preparation of a variety of ketenes has been covered, and an account of the possible mechanisms regarding the [2+2] cycloaddition between ketenes and unsaturated compounds is given.
The synthesis of a family of natural β-lactones called the panclicins, which have all proved to be pancreatic lipase inhibitors, has been performed. The key step in the synthesis of each panclicin is a [2+2] cycloaddition between an aldehyde and an alkyl(trialkylsilyl)ketene in the presence of the Lewis acid EtAlCl2.
The cycloaddition key step has also been applied to the synthesis of valilactone, another natural β-lactone.
Synthesis of the natural product altemicidin, an acaricidal and antitumour agent, has also been attempted. The key step in the synthesis is an intramolecular dipolar cycloaddition, essential in the preparation of the six-membered fused ring.
University of Southampton
1997
Prideaux, Heather Isabel
(1997)
Cycloadditions in the synthesis of biologically active natural products.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The preparation and reactivity of β-lactones is discussed and is followed by a review of the biological activity, structure and synthesis of the natural β-lactones. The preparation of a variety of ketenes has been covered, and an account of the possible mechanisms regarding the [2+2] cycloaddition between ketenes and unsaturated compounds is given.
The synthesis of a family of natural β-lactones called the panclicins, which have all proved to be pancreatic lipase inhibitors, has been performed. The key step in the synthesis of each panclicin is a [2+2] cycloaddition between an aldehyde and an alkyl(trialkylsilyl)ketene in the presence of the Lewis acid EtAlCl2.
The cycloaddition key step has also been applied to the synthesis of valilactone, another natural β-lactone.
Synthesis of the natural product altemicidin, an acaricidal and antitumour agent, has also been attempted. The key step in the synthesis is an intramolecular dipolar cycloaddition, essential in the preparation of the six-membered fused ring.
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Published date: 1997
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Local EPrints ID: 463001
URI: http://eprints.soton.ac.uk/id/eprint/463001
PURE UUID: 1cf4dd9b-5ac8-49aa-8aa1-62fcea40b85d
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Date deposited: 04 Jul 2022 20:36
Last modified: 04 Jul 2022 20:36
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Author:
Heather Isabel Prideaux
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