36025-82-8Relevant academic research and scientific papers
Perfluoroalkylsulfonyl fluoride in organic synthesis: a facile synthesis of 17α-hydroxy steroids
Guo, Peng-Peng,Ding, Kai
, p. 4096 - 4100 (2015/08/03)
Abstract A facile synthesis of 17α-hydroxy steroids with perfluoroalkylsulfonyl fluoride as hydroxyl activating agent was reported. The method features mild (40 °C), rapid (0.5 h), high yield, and high functional group tolerance. Notably, the method is applicable to HCOOH and CF3COOH, unusual and synthetically useful nucleophiles in hydroxyl inversion reaction.
Structure-based design and synthesis of novel potent Na+,K +-ATPase inhibitors derived from a 5α,14α-androstane scaffold as positive inotropic compounds
De Munari, Sergio,Cerri, Alberto,Gobbini, Mauro,Almirante, Nicoletta,Banfi, Leonardo,Carzana, Giulio,Ferrari, Patrizia,Marazzi, Giuseppe,Micheletti, Rosella,Schiavone, Antonio,Sputore, Simona,Torri, Marco,Zappavigna, Maria Pia,Melloni, Piero
, p. 3644 - 3654 (2007/10/03)
The design, synthesis, and biological properties of novel inhibitors of the Na+,K+-ATPase as potential positive inotropic compounds are reported. Following our model of superposition between cassaine and digitoxigenin, digitalis-like
PREPARATION OF UNLABELLED AND 3H>-LABELLED EPITESTOSTERONE AND ITS METABOLITES
Kasal, Alexander,Fuksova, Kveta,Pouzar, Vladimir
, p. 600 - 611 (2007/10/02)
Cold as well as 3H>-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and Λ1-dehydroepitestosterone (XIII).The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.
Efficacious modification of the Mitsunobu reaction for inversions of sterically hindered secondary alcohols
Martin,Dodge
, p. 3017 - 3020 (2007/10/02)
A practical modification of the Mitsunobu protocol for effecting stereochemical inversions of alcohols has been discovered in which use of p-nitrobenzoic acid as the nucleophilic partner results in significantly improved yields with relatively hindered su
Biomimetic Polyene Cyclizations. Participation of the Methylacetylenic Terminator and Nitroalkanes. A Synthesis of Testosterone
Gravestock, Michael B.,Morton, Douglas R.,Boots, Sharon G.,Johnson, William S.
, p. 800 - 807 (2007/10/02)
The aim of this study was to examine nitroalkanes as trapping agents for the presumed intermediary vinyl cation formed in the acid-catalyzed cyclization of allylic alcohols 1, 5, and 8.Treatment of a solution of the allylic alcohols 1, 5, and 8 with excess trifluoroacetic acid in nitroethane resulted in the formation of the isomeric oxime ethers 3, 7, and 10.Confirmation of the trans-fused hydrindan skeleton of 3 was established by oxidative degradation to the known dione 4.The use of nitroethane as the cyclization solvent allows for the formation of syn and anti forms of the oxime ethers, thereby increasing the complexity of the products formed.This problem was eliminated by using 2-nitropropane as the cyclization solvent.Cyclization of 8 in 2-nitropropane with trifluoroacetic acid yielded the oxime ether 12 which was readily converted to diol 13 with lithium aluminuim hydride in refluxing THF.The stereoisomeric mixture of diols was converted, by two different synthetic pathways (see Schemes I and V), into the 17-hydroxypregnan-20-ones 15 and 16 and dl-testosterone benzoate (34).Catalytic reduction of the Δ1 olefinic bond in diol 13, followed by oxidation of the secondary hydroxyl group with N-bromosuccinimide, afforded dl-17α-hydroxy-5β,17β-pregnan-20-one (15) and dl-17β-hydroxy-5β,17α-pregnan-20-one (16).Alternatively, treatment of the diol 13 with periodic acid gave ketone 28 which upon reduction with sodium borohydride and esterification of the resulting hydroxyl group with benzoyl chloride afforded the benzoate 30.Oxidation of 30 with tert-butyl chromate, followed by reduction of the Δ1 olefinic bond, gave ketone 32.Enol acetylation of ketone 32, followed first by bromination, then dehydrobromination, and cleavage of the resulting semicarbazone, resulted in the completion of a facile synthesis of dl-testosterone benzoate (34) in 18percent overall yield from trienynol 8.
