A Domino Dearomative ipso -Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons.

Raji Reddy ChadaAratikumari Suresh PrasadUprety Ajaykumar

Published in: Organic letters (2024)

Herein, we reveal an unprecedented domino annulation of N -benzyl-acrylamides with 1,3-dicarbonyls for the assembly of fused tricyclic alkaloid frameworks incorporating a spirocycle via an alkylation/dearomative ipso -annulation/Michael addition (desymmetrization) sequence. This conversion involves three carbon-carbon bond formations, generating four chiral carbons, including three quaternary carbon centers, in a single diastereomer in one pot under identical reaction conditions. The synthetic potential of this atom-economic method is illustrated by modifications of the functional groups present in the products obtained.

Keyphrases

molecular dynamics
genome wide
single cell
electron transfer
gene expression
mass spectrometry