Molecule of the Month
November 2022
Tropane and Related Alkaloid Skeletons via a Radical
[3+3]-Annulation Process

We have developed a mild and simple protocol for the synthesis of tropane and homotropanes derivatives. The methodology provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity from simple starting materials using visible-light photoredox catalysis.
The method complements the classical Robinson synthesis by allowing to prepare directly the biologically relevant N-arylated skeletons.

This work was carried out in the group of Prof. Philippe Renaud.

References:

  • E. Colson, J. Andrez, A. Dabbous, F. Dénès, V. Maurel, J.-M. Mouesca, P. Renaud;
    "Tropane and related alkaloid skeletons via a radical [3+3]-annulation process"
    Commun. Chem., 2022, 5, 57/1-12; doi:10.1038/s42004-022-00671-x.