Dimethylformamide → (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate (32) (0.20 g, 0.40 mmol), Pd(dba)2 (0.037 g, 0.11 mmol), dppf (0.09 g, 0.2 mmol), Zn(CN)2 (0.057 g, 0.48 mmol) in anhydrous DMF (5.0 mL) was placed in a microwave tube. The vessel was heated at 150° C. and 10 psi for 1 h. The reaction was cooled to room temperature, diluted with EtOAc and washed with water. The organic layer was concentrated to dryness. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1) to yield (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carbonitrile (77) (0.10 g, 67%) as a white solid.

Provenance & Evidence