Water → 2-propanyl (2E)-3-[(2R,5aR,6S,7R,8aS)-6-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-7-(tetrahydro-2H-pyran-2-yloxy)-3,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-2-yl]acrylate

Participants

Reaction Conditions

Reaction Steps

The compound (165 mg) produced in Example 55 was dissolved in DMSO (2 mL), a Wittig reagent (carboisopropoxymethylenetriphenylphosphorane, 218 mg) and 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX, 168 mg) were added, followed by stirring at 50° C. for 5 hours. Ethyl acetate and water were added to the reaction mixture, and insolubles were filtered. Extraction with ethyl acetate, and washing with an aqueous saturated sodium bicarbonate solution and a saline, and drying with anhydrous magnesium sulfate were carried out, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3→80:20) to obtain a titled compound (174 mg) having the following physical property values.

Provenance & Evidence