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Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction

F. Reuß, P. Heretsch – 2020

A divergent approach to the pyrroloquinoline scaffold as present in the class of aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids. The sequence comprises of a [2+2]-photocycloaddition, a Ramberg–Bäcklund contraction, and a strain-promoted formal electrocyclic rearrangement of a bicyclo[2.2.0]hexene and is potentially extendable to pyrroloindole scaffolds as present in the ibophyllidine alkaloids.

Title
Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction
Author
F. Reuß, P. Heretsch
Date
2020
Identifier
DOI: 10.1021/acs.orglett.0c01242
Citation
Org. Lett. 2020, 22, 3956–3959.