Water → HCID 59516396, compound

Participants

Reaction Conditions

Reaction Steps

(2S,3aS,4E,6S,7S,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-7-[(E)-2-formyl-1-methyleth-1-en-1-yl]-6,13a-dimethyl-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (50 mg, 0.09 mmol) was dissolved in a mixed solvent of THF (0.4 ml) and toluene (2.8 ml), and the solution was cooled to −40° C. After addition of pyridine (0.38 ml, 4.73 mmol) and 0.5M toluene solution (1.14 ml, 0.57 mmol) of Tebbe reagent (chlorobis(cyclopentadienyl)-(dimethylaluminum)-methylene titanium), the mixture was stirred at the same temperature for 30 minutes. It was warmed to room temperature and further stirred for one hour. Distilled water (1 ml) was added to the reaction solution, and the reaction solution was diluted with ethyl acetate and washed with distilled water and brine sequentially, and after dried over anhydrous sodium sulfate, the drying agent was filtered off and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=4:1) to obtain the title compound (36.3 mg) as a colorless amorphous substance.

Provenance & Evidence