PhI(OAc)2-mediated One-pot Oxidative Decarboxylation And ...

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Organic & Biomolecular Chemistry

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

Ahmed Kamal,*abc Yellaiah Tangella,a Kesari Lakshmi Manasa,c Manda Sathish,a Vunnam Srinivasulu,a Jadala Chetnac and Abdullah Alarifib Author affiliations

* Corresponding authors

a Medicinal Chemistry & Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India E-mail: [email protected]

b Catalytic Chemistry Research Chair, Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia

c Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500 037, India

Abstract

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).

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DOI https://doi.org/10.1039/C5OB00871A Article type Paper Submitted 30 Apr 2015 Accepted 26 May 2015 First published 26 May 2015

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Org. Biomol. Chem., 2015,13, 8652-8662 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS

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

A. Kamal, Y. Tangella, K. L. Manasa, M. Sathish, V. Srinivasulu, J. Chetna and A. Alarifi, Org. Biomol. Chem., 2015, 13, 8652 DOI: 10.1039/C5OB00871A

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Ahmed Kamal Yellaiah Tangella Kesari Lakshmi Manasa Manda Sathish Vunnam Srinivasulu Jadala Chetna Abdullah Alarifi

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