95716-71-5Relevant articles and documents
Efficient preparation method of delta-canrenone
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, (2020/12/31)
The invention discloses an efficient preparation method of delta-canrenone, and belongs to the technical field of preparation of intermediates of medicines. The method comprises the following steps of: by taking 9 alpha-hydroxyl-4-androstenedione as a raw material, firstly removing 9-site hydroxyl through dehydration reaction to generate delta double bonds, then protecting 3-site carbonyl, then performing epoxidation on 17-site carbonyl, condensing with malonic acid diester to form a lactone ring, and performing oxidative decarboxylation or decarboxylation oxidation reaction to obtain delta-canrenone. According to the method, the raw materials are cheap and easy to obtain, the cost is low, reaction products in all steps are easy to purify, the total mass yield of the final product is higher than 80%, and the method is high in operability, extremely high in commercial competitiveness, suitable for industrial large-scale production and good in economic benefit.
Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone
Zhang, Bin,Chen, Hongli,Feng, Huijin,Li, Yuanchao
experimental part, p. 56 - 59 (2011/03/18)
A new and practical method for a stereoselective construction of a steroid 5α,7α-oxymethylene derivative has been developed and successfully applied to the stereoselective synthesis of eplerenone (8). Starting with available 11α-hydroxyl canrenone (1), eplerenone (8) was synthesised in seven steps with a 48% overall yield.
STEROID SPIROLACTONIZATION
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Page 144-145, (2008/06/13)
A steroid comprising a 17-spirolactone or corresponding open lactone structure is obtained by carbonylation of a 17-alkenyl or 17-alkynyl substrate. A 17-alkenyl intermediate may be prepared by semi-hydrogenation of a 17-alkynyl group. Multiple reaction schemes are disclosed for preparation of a 3-keto-9,11-epoxy-17-spirolactone steroid such as eplerenone. Novel intermediates are also disclosed, as well as steps for forming such novel intermediates, or converting them to further intermediates or products, by semi-hydrogenation, carbonylation, 6,7-dehydrogenation, furylation or other transformations or combinations thereof.
Processes for preparation of 3-keto-7alpha-alkoxycarbonyl-delta-4,5- steroids and intermediates useful therein
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Page 65, (2008/06/13)
Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein:-A-A- represents the group -CHR4-CHR5- or -CR4=CR5- R3, R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, varyloxy;R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical;-B-B- represents the group -CHR6-CHR7- or an alpha- or beta- oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; andR8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R8 and R9 together comprise a carbocyclic or heterocyclic ring structure, or R8 or R9 together with R6 or R7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring.
