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Asymmetric formal synthesis of (+)-cycloclavine†
Jin-Quan Chen,Le-Le Song,Feng-Xing Li,Zi-Fa Shi,Xiao-Ping Cao
Chemical Communications Pub Date : 10/30/2017 00:00:00 , 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.

Graphical abstract: Asymmetric formal synthesis of (+)-cycloclavine
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