Recent approaches to the synthesis of tetrahydrocarbazoles

The tetrahydrocarbazole (THC) motif is ubiquitous in natural products and biologically active compounds. THCs can serve as favorable synthetic intermediates or precursors en-route to desired complex natural products. Despite a considerable number of strategies for the synthesis of THCs that have eme...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 9; pp. 1926 - 1939
Main Authors Chaudhari, Tohasib Yusub, Tandon, Vibha
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 11.03.2021
Subjects
Bioactive compounds
Biological activity
Chemical reactions
Chemists
Cycloaddition
Enantiomers
Intermediates
Natural products
Organic compounds
Ring opening
Synthesis
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Summary:The tetrahydrocarbazole (THC) motif is ubiquitous in natural products and biologically active compounds. THCs can serve as favorable synthetic intermediates or precursors en-route to desired complex natural products. Despite a considerable number of strategies for the synthesis of THCs that have emerged in the last two decades, only a handful of reviews have been published on the subject. Herein, we have summarized synthetic methodologies published in the last ten years for the benefit of organic chemists. The review focuses on non-enantioselective syntheses of THCs, and encompasses ring opening reactions of donor-acceptor cyclopropanes, metal-catalyzed C-C/C-N bond formation, cycloaddition, conjugate addition, and miscellaneous reactions employed for accessing the THC framework. The tetrahydrocarbazole (THC) motif is ubiquitous in natural products and biologically active compounds.
Bibliography:Mr Tohasib Yusub Chaudhari received his B. Pharmacy degree from Govt. College of Pharmacy, Karad in 2012. He completed his M.S. (Medicinal Chemistry) from National Institute for Pharmaceutical Education and Research, Kolkata in 2014. Currently, he is pursuing the Ph.D. under supervision of Prof. Vibha Tandon, at Special Centre for Molecular Medicine, Jawaharlal Nehru University, New Delhi. His research area is the development of catalytic domino reaction for heterocyclic synthesis.
Prof. Vibha Tandon received her Ph.D. in Chemistry from Allahabad University in 1991. Earlier she was a faculty at Ambedkar Centre for Biomedical Research, University of Delhi, later she joined as Associate Professor in Chemistry Department, DU. Currently, she is a professor at the Special Centre for Molecular Medicine, Jawaharlal Nehru University, India. She was awarded Royal Society fellowship to visit MRC, Cambridge in the year 2007. She was Fulbright-Nehru Senior Fellow in 2013 at GSU, Atlanta, USA and DAAD fellow at Radiation Biology Laboratory at ESSEN Medical School, Germany in the year 2012. She is a medicinal chemist working on synthetic methods development on domino reactions, metal-catalyzed and cross-coupling reactions for the construction of heterocyclic rings.
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d0ob02274h