Stereoselective Approach to C-3a Reverse-Prenylated Hexahydropyrrolo[2,3-b]indole Alkaloid

Kumar, Chandan (2022) Stereoselective Approach to C-3a Reverse-Prenylated Hexahydropyrrolo[2,3-b]indole Alkaloid. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Chandan Kumar (17MS034)) 17MS034_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (3MB)

Abstract

Natural compounds containing pyrrolidinoindoline are a rapidly developing class of alkaloids with a wide range of biological properties. Fungi, bryozoans, and other cyanobacteria produce prenylated indole alkaloids, which are a diverse family of natural compounds with a wide range of compositions and biological functions. Hexahydropyrrolo[2,3-b]indoles with an incorporated 1-(1,1-dimethylallyl) substituent at an indoline C-3 quaternary core are a subset of this family of natural compounds. The implementation of this unique substitution arrangement has been termed "reverse prenylation" which differentiates it from the less common isomeric prenylation involving the installation of 1-(3,3-dimethylallyl) substituents. The embedded structures with reversed prenyl groups represent various significant difficulties in the development of synthetic techniques leading to complicated natural products. Compounds in figure 1 are related to naturally occurring C-3a reverse-prenylated hexahydropyrrolo[2,3-b]indole alkaloids. The brevicompannines (BrvA-BrvC) natural product family was discovered to have plant growth regulating properties after being isolated from the culture filtrate of the fungus Penicillium brevicompactum. Brevicompanine A was discovered to have antiviral and cytotoxic effects.2 Amauromine (1d) is a novel alkaloid with vasodilating properties that were discovered by Takase and co-workers from the culture broth species Amauroaucus sp. No. 6237. Because of its structural uniquenessvasodilator, this alkaloid appears to excite synthetic chemists' interest. Brevicompannine B and amauromine (1d) could be prepared through reverse prenylation of bromohexahydropyrroloindole derivative which can be synthesized from the L-tryptophan using a nucleophilic substitution process with prenyl tributylstannane. and biological5 activity as a

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