6901-40-2Relevant articles and documents
Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
Di Chenna, Pablo H.,Veleiro, Adriana S.,Sonego, Juan M.,Ceballos, Nora R.,Garland, M. Teresa,Baggio, Ricardo F.,Burton, Gerardo
, p. 2453 - 2457 (2008/02/13)
A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Δ4-3-keto steroids with a 19-mesylate in the presence of KOH in isopropanol. Three 6,19-cyclopregnanes were prepared (4, 5, 9); in the rat, 6,19-cycloprogesterone (4) and its 21-hydroxy derivative 5 displaced [3H]-dexamethasone from glucocorticoid receptors, the former compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. This journal is The Royal Society of Chemistry.
Convenient preparative routes to 19-hydroxy, 19-oxo-, 19-oic-, and 19-nor-deoxycorticosterone
Terasawa,Okada
, p. 537 - 545 (2007/10/02)
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New Syntheses of 19,21-Dihydropregn-4-ene-3,20-dione, 21-Hydroxy-19-norpregn-4-ene-3,20-dione, and 11β,19,21-trihydroxypregn-4-ene-3,20-dione
Kirk, David N.,Yeoh, Boon Leng
, p. 2945 - 2952 (2007/10/02)
19,21-Dihydroxypregn-4-ene-3,20-dione has been synthesized from 3β-acetoxypregn-5-en-20-one via the "hypoiodite reaction" , and Henbest acetoxylation at C-21; oxidation of the intermediate 21-monoacetate to 19-oxo derivative and alkaline cleavage gave 21-hydroxy-19-norpregn-4-ene-3,20-dione.A similar synthesis of 11β,19,21-trihydroxypregn-4-ene-3,20-dione from 3β-acetoxypregn-5-ene-11,20-dione proceeded through intermediates with the 11β-hydroxy function protected as its acetate.Unusual features mainly of conformational origin were observed in the presence of the 11β-acetoxy substituent; some were helpful to the synthesis, while others led to undesirable side reactions.