Total Syntheses of Chelidonine and Norchelidonine via an Enamide–Benzyne–[2 + 2] Cycloaddition Cascade

Total syntheses of chelidonine and norchelidonine featuring an enamide–benzyne–[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels–Alder reaction.

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 11; pp. 2742 - 2745
Main Authors Ma, Zhi-Xiong, Feltenberger, John B, Hsung, Richard P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.06.2012
Amer Chemical Soc
Subjects
Benzene Derivatives - chemistry
Benzophenanthridines - chemical synthesis
Benzophenanthridines - chemistry
Berberine Alkaloids
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Cyclization
Molecular Conformation
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
HALIDES
INSERTION
DIELS-ALDER REACTIONS
CATALYZED SYNTHESIS
MEDIATED SYNTHESIS
WEITERE ALKALOIDE AUS
MOHNGEWACHSE PAPAVERACEAE
STEREOCONTROLLED SYNTHESIS
ARYNE CHEMISTRY
BENZYNE
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Summary:Total syntheses of chelidonine and norchelidonine featuring an enamide–benzyne–[2 + 2] cycloaddition initiated cascade is described. The cascade includes a pericyclic ring-opening and intramolecular Diels–Alder reaction.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300967a