Recent approaches to the synthesis of tetrahydrocarbazoles
Tohasib Yusub Chaudhari1, Vibha Tandon1
1Special Centre for Molecular Medicine, Jawaharlal Nehru University, New Delhi 110067, India. vtandon@mail.jnu.ac.in.
Abstract:
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.
More Related Videos
Related Concept Videos
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Multiple Halogenation of Methyl Ketones: Haloform Reaction
Cycloaddition Reactions: Overview
Five-Membered Heterocyclic Aromatic Compounds: Overview
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.


