PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I

Iodobenzene diacetate was employed as a mild and efficient reagent for one-pot oxidative decarboxylation of tetrahydro-β-carboline acids and dehydrogenation of tetrahydro-β-carbolines to access the corresponding aromatic β-carbolines. To the best of our knowledge this is the first synthesis of β-car...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-08, Vol.13 (32), p.8652-8662
Main Authors: Kamal, Ahmed, Tangella, Yellaiah, Manasa, Kesari Lakshmi, Sathish, Manda, Srinivasulu, Vunnam, Chetna, Jadala, Alarifi, Abdullah
Format: Article
Language:English
Subjects:
Acetates - chemistry
Carbolines - chemical synthesis
Carbolines - chemistry
Decarboxylation
Harmine - analogs & derivatives
Harmine - chemical synthesis
Harmine - chemistry
Iodobenzenes - chemistry
Molecular Structure
Oxidation-Reduction
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Summary:Iodobenzene diacetate was employed as a mild and efficient reagent for one-pot oxidative decarboxylation of tetrahydro-β-carboline acids and dehydrogenation of tetrahydro-β-carbolines to access the corresponding aromatic β-carbolines. To the best of our knowledge this is the first synthesis of β-carbolines via a one-pot oxidative decarboxylation at ambient temperature. The utility of this protocol has been demonstrated in the synthesis of β-carboline alkaloids norharmane (2o), harmane (2p), eudistomin U (9) and eudistomin I (12).
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00871a