Asymmetric total synthesis of the iridoid beta-glucoside (+)-geniposide via phosphine organocatalysis.
Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.
Jones
Regan A
RA
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Krische
Michael J
MJ