54274-75-8Relevant academic research and scientific papers
Facile acetylation of alcohols, ethers and ketals with catalytic FeCl3 in AcOH
Sharma,Mahalingam,Nagarajan,Ilangovan,Radhakrishna, Palakodety
, p. 1200 - 1202 (1999)
A simple and efficient protocol for the conversion of alcohols, ethers and ketals to acetates using catalytic FeCl3(5mol%) in AcOH, or AcOH (3eq) in CH2Cl2 in very high yield is reported. A variety of other acids such as CF3CO2H, HCO2H, CH2=CHCO2H, CH3CH2CO2H, CH3(CH2)2CO2H have also been utilised for the acylation of alcohols successfully.
A simple and convenient synthesis of 2-methoxyestradiol from estrone
Prakasham,Shanker, Karuna,Negi, Arvind S.
scheme or table, p. 467 - 470 (2012/05/19)
A simple and straightforward synthesis of 2-methoxyestradiol have been achieved in nine synthetic steps with 21% of overall yield. Being a convenient process, it can be upscaled to industrial process.
Synthesis of chalcone derivatives on steroidal framework and their anticancer activities
Saxena, Hari Om,Faridi, Uzma,Kumar,Luqman, Suaib,Darokar,Shanker, Karuna,Chanotiya, Chandan S.,Gupta,Negi, Arvind S.
, p. 892 - 900 (2008/02/13)
Chalcone derivatives on estradiol framework have been synthesized. Some of the derivatives showed potent anticancer activity against some human cancer cell lines. Compounds 9 and 19 showed potent activity against MCF-7, a hormone dependent breast cancer cell line. Chalcone 7 was further modified to the corresponding indanone derivative (19) using the Nazarov reaction, which showed better activity than the parent compound against the MCF-7 breast cancer cell line. Active anticancer derivatives were also evaluated for osmotic hemolysis using the erythrocyte as a model system. It was observed that chalcone derivatives showing cytotoxicity against cancer cell lines did not affect the fragility of erythrocytes and hence may be considered as non-toxic to normal cells.
Combined epimerisation and acylation: Meerwein-ponndorf-verley-oppenauer catalysts in action
Klomp, Dirk,Djanashvili, Kristina,Svennum, Nina Cianfanelli,Chantapariyavat, Nuttanun,Wong, Chung-Sing,Vilela, Filipe,Maschmeyer, Thomas,Peters, Joop A.,Hanefeld, Ulf
, p. 483 - 489 (2007/10/03)
A practical racemisation-epimerisation method for chiral secondary alcohols has been developed. Meerwein-Ponndorf-Verley-Oppenauer catalysts such as neodymium(III) isopropoxide are able to racemise these alcohols with retention of other stereocentres in the molecule. This is particularly useful for the recycling of the undesired products of kinetic resolutions of alcohols. By combination of such a racemisation with an acylation using isopropenyl or ethoxyvinyl esters as acyl donors, a fast straightforward recycling of starting materials may be achieved. The combined epimerisation and acylation process is demonstrated for the steroid estradiol methyl ether.
REDUCTIVE DESULFONYLATION OF PHENYL SULFONES BY SAMARIUM(II) IODIDE-HEXAMETHYLPHOSPHORIC TRIAMIDE
Kuenzer, H.,Stahnke, M.,Sauer, G.,Wiechert, R.
, p. 1949 - 1952 (2007/10/02)
Samarium(II) iodide in tetrahydrofuran reductively desulfonylates phenyl sulfones in the presence of hexamethylphosphoric triamide.This transformation is illustrated here for ten substrates, which include secondary alicyclic, β-hydroxy, vicinal bis-, and α,β-unsaturated sulfones.
DIRECT, HIGH-YIELD TRANSFORMATION OF TETRAHYDROPYRANYL ETHERS TO ACETATES
Bakos, Tamas,Vincze, Iren
, p. 523 - 528 (2007/10/02)
The practically quantitative transformation of steroidal tetrahydropyranyl ethers to acetates with acetyl chloride in aprotic solvents is described.
Synthesis of C-2 and C-4 deuterium-labeled estradiol-17β
Ferraboschi,Ravasi,Santaniello
, p. 777 - 782 (2007/10/02)
Estradiol-17β labeled with deuterium in the positions 2 or 4 can be prepared from 2-chloromercurio-1,3,5(10)-estratriene-3,17β -diol 3-methyl ether 17-acetate or 4-chloromercurio-1,3,5(10)-estratriene-3,17β -diol, respectively, in refluxing CH3COO2H/2H2O. The same reaction performed on 4-acetoxymercurio1,3,5(10)-estratriene-3,17β -diol afforded 2,4-dideuterio-estradiol-17β in good yields.
BORON ANNULATION: TOTAL SYNTHESIS OF (+/-)-ESTRONE METHYL ETHER
Bryson, Thomas A.,Reichel, Curtis J.
, p. 2381 - 2384 (2007/10/02)
The stereoselective hydroboration and carbonylation of highly functionalized 1,4-dienes affords trans-hydrindanones in good yield.These trans-hydrindanones are synthons for norpregnenolone, estrone and related estradiol derivatives.
