89376-69-2Relevant academic research and scientific papers
Synthesis of 1,11α-ethano corticosteroids
Wieland,Kalvoda
, p. 5603 - 5606 (1983)
11α-Formyl-methyl derivative 5 of prednisolone has been reductively cyclized to give the versatile pentacyclic intermediates 7 and 9 of novel 1,11α-ethano-bridged corticosteroid analogues.
Total Synthesis of Cortisol: Application to Selective Deuteriation at C-1 and C-19
Minagawa, Kazuo,Furuta, Takashi,Kasuya, Yasuji,Fujino, Akiharu,Avery, Mitchell A.,Tanabe, Masato
, p. 587 - 592 (2007/10/02)
An 11-step total synthesis of cortisol and its application to selective deuteriation at the 19-methyl and the C-1 positions is described.The dihydroxy acetone group at C-17 of prednisone (3) was protected as the bismethylenedioxy derivative (4) and degraded to the ring C/D fragment, oxoindanylpropionic acid (2), by Birch reduction followed by ozonolysis.The reaction of deuterioisopropenyl anion with compound (2) followed by dehydration, cyclisation, and osonolysis produced -4,5-seco-17α,20;20,21-bismethylenedioxypregnane-3,5,11-trione .Cyclisation of (16a) in KOH-MeOH affordedthe bismethylenedioxy cortisone (17), wich upon reduction with KBH4 gave the desired (2)H5 cortisol (19).
