Asymmetric formal synthesis of (+)-cycloclavine

Chem Commun (Camb). 2017 Nov 30;53(96):12902-12905. doi: 10.1039/c7cc08044a.

Abstract

The asymmetric synthesis of Szántay's amine (+)-2, the pivotal precursor for direct access to (+)-cycloclavine (1), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman's sulfinimine and rhodium-catalysed isomerization of the C[double bond, length as m-dash]C bond.