Synthetic Approaches to Trimeric Tryptamine Alkaloid, Psychotrimine

Kumar, Avneesh (2022) Synthetic Approaches to Trimeric Tryptamine Alkaloid, Psychotrimine. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Avneesh Kumar (17MS039)) 17MS039_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (1MB)

Abstract

Naturally occurring polymeric indole alkaloids containing hexahydropyrrolo[2,3-b]indole core, and uncommon N1-C3a linkage between the pyrroloindole unit and indole ring have considerably piqued the interest of synthetic chemists because of their unique structural features and excellent biological activities. There are a number of naturally occurring alkaloids of this class which contains different number of indole and hexahydropyrrolo indole units such as psychotriasine (1a), psychotrimine (1b), psychotetramine (1c) (Figure 1). Especially, due to the high bond energy of C-N with compared to C-C bond and the special electronic arrangement in the indole ring, indoles prefer oxidative dimerization at carbon center (C3) rather than nitrogen, the formation of this unique bond is particularly difficult, for this the total synthesis of psychotriasine (1a) and related analogues possessing a C-N linkage are very much challenging and 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. Biosynthetically, the polymeric hexahydropyrrolo[2,3-b]indole alkaloids are believed to be originated from L-tryptophan following the radical coupling and radical cyclization with the help of enzyme P450, sequentially decarboxylation in the presence of decarboxylase enzyme. In our hypothesis, we have constructed the 3a-bromo-hexahydropyrrolo[2,3-b] indole moiety electrochemically, and tried to couple with tryptamine unit in the presence of base.

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