Реакция #3127

Уравнение реакции

(4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one

(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene

tert-butyllithium

benzoic anhydride

1-hexynylcopper

→

methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate

Выход 55.4%

Растворители

hexamethylphosphorous triamide

Условия реакции

Методика

Using as the materials and reagents (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (442 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 1-hexynylcopper (174 mg), hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one (373 mg, 1.0 mmol), and benzoic anhydride (661 mg), the same procedure was performed as in Example 1 to obtain methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg, 33%).

Источник