The Selective Protection of the 3-Ketone Functions of Steroids as Heptafluoro-p-tolyl Enol Ethers
Conjugated and unconjugated 3-ketone functions in steroids react with octafluorotoluene at above 100 deg C in the presence of caesium fluoride to give heptafluoro-p-tolyl enol ethers.The related but unusually reactive Wieland-Miescher ketone (11) reacted at room temperature in the presence of tetra-n-butylammonium fluoride.Enones were regenerated from their derivatives by acidic hydrolysis.Hydrolysis of the derivative (10) of 4,5α-dihydroxytestosterone was slu but sodium methoxide regenerated the parent steroid.The methods have been applied in a synthesis of deuterium-labelled testosterone.
Jarman, Michael,McCague, Raymond
p. 1129 - 1134
(2007/10/02)
Heptafluoro-p-tolyl as a Selective Protecting Group for the Enone Function of Androst-4-ene-3,17-dione: Application to the Preparation of Deuterium-labelled Testosterone
Octafluorotoluene reacts with the enone function of androst-4-ene-3,17-dione in the presence of caesium fluoride to give specifically a 3,5-dienol ether which has been used to prepare deuterium-labelled testosterone.
Jarman, Michael,McCague, Raymond
p. 635 - 636
(2007/10/02)
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