Catalytic Enantioselective Allylation of Acetylenic
Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis:
Formal Synthesis of Fostriecin
posted on 2021-04-23, 14:38authored byShigenobu Umemiya, Masahiro Terada
An
enantioselective allylation of silyl-substituted acetylenic
aldehydes by chiral phosphoric acid (CPA)/transition metal cooperative
catalysis was developed. Enantioenriched homoallylic propargyl alcohols
were obtained in good yields with excellent enantioselectivities (>99%
ee) under mild conditions. Moreover, the shortest formal synthesis
of fostriecin was achieved by the present enantioselective allylation
protocol as the key step. The known intermediate of fostriecin reported
by McDonald and co-worker was synthesized in only nine steps in 39%
total yield.