A synthetic approach to geodiamolides A and B
A synthetic approach to geodiamolides A and B
A synthetic approach to the marine cyclodepsipeptides Geodiamolide A and B is described. The synthesis is based on the construction of two key fragments: a tripeptide and a polyketide. Attempts to reproduce published procedures for the synthesis of the tripeptide were complicated by problems in protecting group manipulation and some discrepancies in spectroscopic data. The synthesis of the polyketide fragment (Philip Ashworth's route) involved a novel method for the chromatographic resolution of tetrahydropyran-2-ones which was shown to be general. Union of the tripeptide and polyketide fragments was successful and gave an advanced intermediate which had previously been converted to Geodiamolide A or B corresponding to the aromatic ring halogens.
University of Southampton
Belagali, Shiddappa Lagamappa
027280c6-662a-47b2-ab87-abaaabce6acd
1992
Belagali, Shiddappa Lagamappa
027280c6-662a-47b2-ab87-abaaabce6acd
Belagali, Shiddappa Lagamappa
(1992)
A synthetic approach to geodiamolides A and B.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
A synthetic approach to the marine cyclodepsipeptides Geodiamolide A and B is described. The synthesis is based on the construction of two key fragments: a tripeptide and a polyketide. Attempts to reproduce published procedures for the synthesis of the tripeptide were complicated by problems in protecting group manipulation and some discrepancies in spectroscopic data. The synthesis of the polyketide fragment (Philip Ashworth's route) involved a novel method for the chromatographic resolution of tetrahydropyran-2-ones which was shown to be general. Union of the tripeptide and polyketide fragments was successful and gave an advanced intermediate which had previously been converted to Geodiamolide A or B corresponding to the aromatic ring halogens.
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Published date: 1992
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Local EPrints ID: 461246
URI: http://eprints.soton.ac.uk/id/eprint/461246
PURE UUID: 2c542a47-cb20-4fe8-a621-a8d3a7912d67
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Date deposited: 04 Jul 2022 18:41
Last modified: 23 Jul 2022 01:08
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Author:
Shiddappa Lagamappa Belagali
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