Synthesis of the 16α,17α,21-Trimethyl Corticosteroid Rimexolone from Prednisolone

Expeditious Synthesis of Hippuristanol and Congeners with Potent Antiproliferative Activities

“…Removal of the 21‐OH in 8 was achieved via tosylate formation, giving 9 (91 %), and replacement of the tosylate with iodide, followed by reduction (NaI, acetone, reflux; then AcOH, 65 °C),8 furnishing the desired 10 in 98 % yield. Under the action of semicarbazide in aqueous acetic acid at 80 °C,8c, 9 the α‐hydroxy‐ketone 10 was converted to enone 11 in 83 % yield. A rearranged compound ( S1 )10 was detected in trace amount, which had been the major product upon treatment of 10 with SOCl 2 in pyridine at room temperature 11.…”

11β,17aα-Dihydroxy-17aβ-methyl-D-homoandrosta-1,4-diene-3,17-dione monohydrate

“…E65, o935 [doi:10.1107/S1600536809010770] 11β,17aα-Dihydroxy-17aβ-methyl-D-homoandrosta-1,4-diene-3,17-dione monohydrate Ya Qiu, Ying Chen and Peng Xia S1. Comment 21-Methyl-11β,17α-dihydroxy-1,4-pregnadien-3,20-dione derivatives are intermediates in the synthesis of steroid agents (Conrow, 1999). We tried to prepare 21-methyl-11β,17α-dihydroxy-1,4-pregnadien-3,20-dione by 21-methylation of 11β,17α-dihydroxy-21-chloro-1,4-pregnadien-3,20-dione with organic metal reagent.…”

11β-Hydroxypregna-1,4,16-triene-3,20-dione

“…The title compound (I), which can be made from 16dehydroprogesterone in a multi-step process (Herzog et al, 1959), is an important steroid derivative. It has been used in the syntheses of some corticosteroids (Conrow, 1999). Its 1 H and 13 C NMR spectra have previously been used to establish the atomic connectivity (Kirk et al, 1990).…”