Total synthesis of (18S)- and (18R)-homolargazole by rhodium-catalyzed hydrocarboxylation

Abstract

Homolargazole derivatives, in which the macrocycle of natural largazole is extended by one methylene group, were prepared by the recently developed rhodium-catalyzed hydrocarboxylation reaction onto allenes. This strategy gives access to both the (18S)- and (18R)-stereoisomers in high stereoselectivity under ligand control.

Keywords: macrocyclic compounds; medicinal chemistry; rhodium; stereoselective catalysis; synthetic drugs.