Synthesis of the ABC Core of Alkaloids with a [5-6-7] Azatricyclic Scaffold Via Ring Expansion of Azabicyclic and Azatricyclic Building Blocks

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Jul 1

PMID 38950520

Authors

Claudia Marques

David Gonzalez-Lizana

Faiza Diaba

Josep Bonjoch

Affiliations

Soon will be listed here.

Abstract

The [5-6-7] azatricyclic ABC core, found in several alkaloids, has been synthesized through a novel route involving ring expansion of a perhydroindolone to afford the AC ring system and a radical B ring closure as key steps. The level of functionalization of the reported octahydro-1,7-ethanocyclohepta[]pyrroles suggests that they can serve as valuable building blocks in this alkaloid field. Also reported is the first synthesis of homomorphans by the ring enlargement of 2-azabicyclo[3.3.1]nonanes.

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