Toward the stereochemical assignment and synthesis of hemicalide: DP4f GIAO-NMR analysis and synthesis of a reassigned C16-C28 subunit.
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Peer-reviewed
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Article
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Authors
MacGregor, Callum I
Han, Bing Yuan
Goodman, Jonathan M
Abstract
Using the DP4f GIAO-NMR method, the stereochemistry of hemicalide was computationally analysed, resulting in a reassignment at C18 as supported by improved NMR shift correlations with a model C13-C25 fragment 23. An advanced C16-C28 subunit 6 of this potent anticancer agent was then synthesised with the revised 18,19-syn relationship.
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Keywords
0305 Organic Chemistry
Journal Title
Chem Commun (Camb)
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Journal ISSN
1359-7345
1364-548X
1364-548X
Volume Title
52
Publisher
Royal Society of Chemistry (RSC)
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Sponsorship
We thank the EPSRC for financial support (studentship to CIM) and the National Mass Spectrometry Centre (Swansea) for mass spectra.