Synthetic Approaches to Pseudophrynamine A

Kumar, Raman (2022) Synthetic Approaches to Pseudophrynamine A. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Raman Kumar (17MS086)) 17MS086_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (2MB)

Abstract

Cyclotryptamine alkaloids are a vast family of naturally occurring secondary metabolites generated from L-tryptophan, encompassing the hexahydropyrrolo[2,3-b]indole ring framework. The characteristic structural feature of a large number of natural compounds is a hexahydropyrrolo[2,3-b]indole ring with a carbon substituent at the C-3a position.The synthetic analogues of these cyclotryptamine alkaloids exhibit physiological activities, such as inhibition of acetylcholinesterase, butyrylcholinesterase and smooth-muscle relaxant activity etc. Therefore, devising synthetic strategies for these alkaloids is not only interesting from an academic point of view but also provides the opportunity to further test their biological potential for societal impact. These alkaloids are closely related to naturally occurring C-3a prenylated hexahydropyrrolo[2,3- b]indole alkaloids (Fig.1) like pseudophrynaminol (2b) and pseudophrynamine A (3), which were isolated from the skin of the Australian frog Pseudophryne coriacea and possess several biological activities including neurotoxic activity, anti-cancer drugs, muscle relaxants, potassium channel inhibitors and act as a potent inhibitor of the ganglionic receptor. Due to their extraordinary structural architecture and biological relevance, the entire synthesis of these natural products has drawn the awareness of the synthetic community. In this thesis, entitled " Synthetic Approaches to Pseudophrynamine A " we have focussed on the f

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