Potassium Phosphate, Tribasic → (1R,10R,11S,16S)-5-methoxy-1,3,11,15,15-pentamethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene

Participants

Reaction Conditions

Reaction Steps

In a sealed tube was placed (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 (Compound No. 32) (0.098 g, 0.20 mmol), trimethylboroxine (0.050 g, 0.40 mmol), K3PO4 (0.085 g, 0.40 mmol), Pd(Ph3P)4 (0.046 g, 0.04 mmol) and dioxane (4 mL). The vessel was degassed for 5 min, then sealed and stirred at 100° C. for 16 h. The reaction was cooled to room temperature, diluted with EtOAc and washed with brine. The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 95:5) gave (1R,10R,11S,16S)-5-methoxy-1,3,11,15,15-pentamethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 33) (0.060 g, 83%) as a white foam. 1H NMR (CDCl3): δ 6.46 (m, 1H), 6.39 (m, 1H), 3.71 (s, 3H), 2.98-2.80 (m, 3H), 2.50 (s, 3H), 1.95-1.37 (m, 8H), 1.37 (s, 3H), 1.20-1.00 (m, 2H), 0.94 (s, 3H), 0.90 (m, 1H), 0.86 (s, 3H), 0.84 (s, 3H). MS m/z 359 (C23H34OS+H+).

Provenance & Evidence