Oxidative approaches to the synthesis of bis-Tetrahydrofuran Annonaceous Acetogenins
Oxidative approaches to the synthesis of bis-Tetrahydrofuran Annonaceous Acetogenins
Two bis-THF Annonaceous Acetogenin structures were synthesised, one of which corresponded to the cytotoxic antitumour compound membranacin 3.19. Both derived from key epoxide intermediate 6.7, which was synthesized via the chiral auxiliary directed oxidative cyclisation of 1,5,9-trienedioate 4.44 by potassium permanganate. The second THF ring was installed using a Sharpless asymmetric epoxidation and epoxide opening strategy. A number of intermediates were designed with the potential for future library synthesis of natural product analogues.
The combination of the permanganate oxidation and Kennedy’s perrhenate cyclisation of bis-homoallylic alcohols was used to synthesise simple bis-THF model 7.2. This combined strategy allows access to the acetogenin bis-THF core.
University of Southampton
Head, Geoffrey Douglas
18fe4a7a-9b23-47c0-93e1-cc8f0ae62184
2004
Head, Geoffrey Douglas
18fe4a7a-9b23-47c0-93e1-cc8f0ae62184
Head, Geoffrey Douglas
(2004)
Oxidative approaches to the synthesis of bis-Tetrahydrofuran Annonaceous Acetogenins.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
Two bis-THF Annonaceous Acetogenin structures were synthesised, one of which corresponded to the cytotoxic antitumour compound membranacin 3.19. Both derived from key epoxide intermediate 6.7, which was synthesized via the chiral auxiliary directed oxidative cyclisation of 1,5,9-trienedioate 4.44 by potassium permanganate. The second THF ring was installed using a Sharpless asymmetric epoxidation and epoxide opening strategy. A number of intermediates were designed with the potential for future library synthesis of natural product analogues.
The combination of the permanganate oxidation and Kennedy’s perrhenate cyclisation of bis-homoallylic alcohols was used to synthesise simple bis-THF model 7.2. This combined strategy allows access to the acetogenin bis-THF core.
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Published date: 2004
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Local EPrints ID: 465288
URI: http://eprints.soton.ac.uk/id/eprint/465288
PURE UUID: e036ea74-e3af-47d3-8157-1155d5255546
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Date deposited: 05 Jul 2022 00:35
Last modified: 16 Mar 2024 20:05
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Author:
Geoffrey Douglas Head
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