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ChemInform Abstract: Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent: Leading to Galanthamine-Type Amaryllidaceae Alkaloids.

✍ Scribed by Y. KITA; M. ARISAWA; M. GYOTEN; M. NAKAJIMA; R. HAMADA; H. TOHMA; T. TAKADA

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199907246

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✦ Synopsis

Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:

Leading to Galanthamine-Type Amaryllidaceae Alkaloids.

-A versatile procedure for the synthesis of galanthamine-type Amaryllidaceae alkaloids, e.g. narwedine (VII) and galanthamine (VIII), is developed based on the phenyliodine(III) bis(trifluoroacetate)-induced intramolecular phenolic coupling of norbelladine derivatives. This method is applied to the first total synthesis of sanguinine (IX).

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