Regiospecific and Stereoselective Syntheses of (±) Morphine, Codeine, and Thebaine via a Highly Stereocontrolled Intramolecular 4 + 2 Cycloaddition Leading to a Phenanthrofuran System

Regiospecific and Stereoselective Syntheses of (±) Morphine, Codeine, and Thebaine via a Highly Stereocontrolled Intramolecular 4 + 2 Cycloaddition Leading to a Phenanthrofuran System

Total syntheses of the morphine alkaloids are described that use a direct stereoselective formation of the phenanthrofuran system via an intramolecular 4 + 2 cycloaddition of a diene tethered to the 4-position of a 7-methoxybenzofuran-3-carboxylic acid ester.

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Veröffentlicht in:Journal of the American Chemical Society 2009-08, Vol.131 (32), p.11402-11406
Hauptverfasser: Stork, Gilbert, Yamashita, Ayako, Adams, Julian, Schulte, Gary R., Chesworth, Richard, Miyazaki, Yoji, Farmer, Jay J.
Format: Artikel
Sprache:eng
Schlagworte:
Codeine - chemical synthesis
Molecular Structure
Morphine - chemical synthesis
Stereoisomerism
Thebaine - chemical synthesis
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Zusammenfassung:Total syntheses of the morphine alkaloids are described that use a direct stereoselective formation of the phenanthrofuran system via an intramolecular 4 + 2 cycloaddition of a diene tethered to the 4-position of a 7-methoxybenzofuran-3-carboxylic acid ester.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9038505