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General Procedure F. To a solution of 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid (Compound 28, 242 mg, 0.78 mmol) under argon was added methyllithium (3.0 M in diethoxymethane, 5.2 ml, 15.7 mmol) at room temperature. The reaction was stirred for 4 h and was quenched with 1 M HCl, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-50% EtOAc-hexanes to yield 1-(1-benzyl-5-hydroxy-2-isopropyl-1H-indol-3-yl)ethanone (Compound 29) as a yellow solid.

1. customwas quenched with 1 M HCl
2. extractionextracted with EtOAc
3. washThe organic layer was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography on silica gel eluting with 0-50% EtOAc-hexanes