The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D

The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D

The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland–Claisen/Diels–Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D...

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Veröffentlicht in:Journal of organic chemistry 2014-10, Vol.79 (20), p.9740-9747
Hauptverfasser: Gordon, Jonny R, Nelson, Hosea M, Virgil, Scott C, Stoltz, Brian M
Format: Artikel
Sprache:eng
Schlagworte:
Artemisinins - chemical synthesis
Artemisinins - chemistry
Cycloaddition Reaction
Indicators and Reagents - chemistry
Molecular Structure
Palladium - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Stereoisomerism
Zinc - chemistry
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Zusammenfassung:The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland–Claisen/Diels–Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three rings, two all-carbon quaternary centers, and four tertiary stereocenters from a monocyclic, achiral precursor.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501924u