A new and short synthesis of racemic cis-clavicipitic acid was achieved by taking advantage of the double nucleophilic character of indole-4-pinacolboronic ester. Key to the success of the synthesis were an efficient and selective C-3 indole Friedel–Crafts alkylation and the development of an unprecedented intramolecular rhodium-catalyzed 1,2-addition of an aryl pinacolboronic ester to an unactivated imine.

Synthesis of (±)-cis-Clavicipitic Acid by a Rh(I)-Catalyzed Intramolecular Imine Reaction

BARTOCCINI, FRANCESCA;MARI, MICHELE;PIERSANTI, GIOVANNI
2014-01-01

Abstract

A new and short synthesis of racemic cis-clavicipitic acid was achieved by taking advantage of the double nucleophilic character of indole-4-pinacolboronic ester. Key to the success of the synthesis were an efficient and selective C-3 indole Friedel–Crafts alkylation and the development of an unprecedented intramolecular rhodium-catalyzed 1,2-addition of an aryl pinacolboronic ester to an unactivated imine.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2594178
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