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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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 131; no. 32; pp. 11402 - 11406
Main Authors Stork, Gilbert, Yamashita, Ayako, Adams, Julian, Schulte, Gary R., Chesworth, Richard, Miyazaki, Yoji, Farmer, Jay J.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.08.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Codeine - chemical synthesis
Molecular Structure
Morphine - chemical synthesis
Physical Sciences
Science & Technology
Stereoisomerism
Thebaine - chemical synthesis
ASYMMETRIC-SYNTHESIS
PRACTICAL SYNTHESIS
CYCLIZATIONS
ALDEHYDE
ENANTIOSELECTIVE SYNTHESIS
TITANIUM(IV) ISOPROPOXIDE
RING
FORMAL TOTAL-SYNTHESIS
OPIUM-ALKALOIDS
(-)-MORPHINE
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja9038505