A dried vial (4 mL) with triflate (0.038 g, 0.082 mmol, 1.0 equiv),
tetrakis[triphenylphosphine]palladium (0.142 g, 0.123 mmol, 1.5 equiv)
and copper(I) chloride (0.014 g, 0.123 mmol, 1.5 equiv) was evacuated
and refilled with carbon monoxide three times. To this vial was added
degassed dimethyl sulfoxide (150 micro L), and the mixture was heated to 55
°C. A solution of stannane (0.028 g, 0.098 mmol, 1.2 equiv) in degassed dimethyl
sulfoxide (100 micro L) was added at same temperature. The suspension was
stirred at 55 °C for 45 min. The mixture was then cooled to 23 °C and
directly purified by silica gel column chromatography (gradient 10% ->
15% ethyl acetate-hexanes) to give enome and as colorless oil (0.025 g, 66%):
Rf = 0.21 (40% ethyl acetate-hexanes)
(No Glossary was required
Stille coupling reaction has been used to create natural products such as chloropeptin, an anti HIV agent, and apoptolidin, a compound involved in apoptosis.
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