Efficient Approach to Dimeric Hexahydropyrrolo[2,3-b] indole Alkaloids

Raj, Anoushka (2022) Efficient Approach to Dimeric Hexahydropyrrolo[2,3-b] indole Alkaloids. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Anoushka Raj (17MS067)) 17MS067_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (2MB)

Abstract

The cyclotryptamine alkaloids are a family of indole alkaloids which comprise the hexahydropyrrolo[2,3-b]indole ring framework. Along with that, they display in various kinds of structural formats. At the C-3a position comprising a carbon substituent in hexahydropyrrolo[2,3-b]indole ring makes it a large class of secondary metabolites, derived from L-tryptophan and its derivatives. To develop the naturally occurring, dimeric hexahydropyrrolo[2,3-b]indole alkaloids efficient electrochemical strategy is reported. The mechanism to synthesize the same involves a Proton Coupled Electron Transfer (PCET) pathway which involves one-electron oxidation along with subsequent proton transfer which generates a neutral radical and thus two radicals combined to form the dimerized product. Finally, a formal total syntheses of (±)-psychotriadine (1), (±)- folicanthine (2b), (±)-calycanthine (3) (Scheme 1) have been shown using electrochemical oxidation followed by dimerization.

Actions (login required)

View Item