Tin tetrachloride → (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

Participants

Reaction Conditions

Reaction Steps

A solution of (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]-methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (13-1) (1.2 g, 3.2 mmol) in CH2Cl2 (85 mL) was cooled to −78° C. under N2. To the mixture, a solution of SnCl4 (1.5 mL) in CH2Cl2 (15 mL) was added dropwise. The mixture was stirred at −78° C. for 3 h. The dry ice bath was removed and stirring at room temperature continued for 2 h. The reaction mixture was quenched with water and the organic layer was separated and concentrated to dryness. The crude product was purified by flash chromatography on silica gel (Hexanes/Toluene, 2:1) 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 (51) (1.0 g, 93% yield) as a white solid. Regioisomer (52) was also obtained as shown in Example 26.

Provenance & Evidence