10.1016/j.tet.2009.02.051
The study focuses on the novel chemistry of β-carbolines, specifically exploring the synthesis of polycyclic scaffolds through various chemical reactions. β-carbolines are heterocyclic compounds found in numerous natural alkaloids with diverse biological activities, making them of interest for pharmaceutical applications. The researchers utilized ring-closing metathesis (RCM) and combined it with other cyclization processes such as Diels-Alder reactions to generate complex molecular structures in a single synthetic step. Chemicals used in the study include allyl-, vinyl-, ethynyl-, and propargyl-b-carbolines as substrates, as well as Grignard reagents and various catalysts like [Ru]-I, [Ru]-II, and [Ru]-III for metathesis reactions. Additionally, compounds like dimethyl acetylenedicarboxylate (DMAD) and dimethyl maleate were employed as dienophiles in Diels-Alder reactions. The purpose of these chemicals was to functionalize β-carbolines and construct more complex heterocycles, which could potentially lead to the development of new drugs with various therapeutic properties. The study also observed novel domino processes and rearrangements, such as Stevens rearrangement, providing insights into the complex polycyclic chemistry of β-carbolines.
10.1016/S0040-4039(02)02336-5
The research focuses on the synthesis of a new nitrone derived from C2 symmetric piperidine, which is used for the creation of hydroxylated indolizidinones. The purpose of this study was to develop an alternative synthetic pathway to these biologically active molecules, which are known as glycosidase inhibitors. The researchers achieved this by oxidizing a C2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, using C-phenyl-N-phenylsulfonyloxaziridine. The resulting nitrone was too unstable for isolation and was therefore reacted in situ with dimethyl maleate, yielding a major adduct that was transformed into a protected dihydroxyindolizidinone. The conclusions of the research indicate that the synthetic process starting from a C2 symmetric piperidine can be considered an alternative method for synthesizing indolizidinones with a precise substitution pattern on the six-membered ring, despite the limited stability of the nitrone. Key chemicals used in this process include C-phenyl-N-phenylsulfonyloxaziridine, dimethyl maleate, and various reagents for the protection and oxidation steps.