34635-41-1Relevant articles and documents
A facile total synthesis of drospirenone isomers containing 14β-hydrogen configuration
Wan, Wen,Ma, Guobin,Gao, Wei,Wang, Jing,Li, Lei,Rao, Shangqin,Zheng, Chunfang,Jiang, Haizhen,Deng, Hongmei,Hao, Jian
, p. 6597 - 6603 (2013/09/24)
A facile strategy for the preparation of two isomeric drospirenones 13 and 16 possessing a 14β-hydrogen was developed, using 3β-hydroxyandrost-5- en-17-one as the starting material. The total synthetic route involves eight steps, giving 2% overall yield. The structures of the main compounds 11, 13, 14 and 16 were determined by single crystal XRD analysis.
Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data
Baranovskii,Bolibrukh,Gromak
experimental part, p. 1877 - 1885 (2012/01/07)
On the basis of dehydroepiandrosterone through the δ14- and δ 15-androst-17-ones a series of androsta-14,16-dienyl acetates was obtained, the key compounds in the synthesis of 14-substituted steroids. By the methods of two-dimensional NMR spectroscopy the structure of compounds was proved and a full assignment of signals in the 1H and 13C NMR spectra was performed. With the use of tandem mass spectrometry the main directions of fragmentation of protonated molecules of the synthesized ketones and dienyl acetates were studied.
Chemical process
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, (2008/06/13)
Saturated organic compounds containing a hydrogen atom bound to a tertiary carbon atom may be electrophilically fluorinated by reaction with an electrophilic fluorinating agent such as molecular fluorine or trifluoromethyl hypofluorite under conditions whereby the formation of free fluorine radicals is suppressed, e.g. by the presence of a free radical inhibitor such as oxygen or nitrobenzene, the reactants being substantially homogeneously dispersed in a liquid medium, e.g. a solvent medium such as fluorotrichloromethane or chloroform/fluorotrichloromethane, so that the said hydrogen atom is electrophilically replaced by a fluorine atom. The fluoroination is highly selective and, in the case of complex substrates such as saturated steroids which contain a number of tertiary C--H bonds, may be substantially completely confined to replacement of the hydrogen atom at the tertiary carbon atom which has the highest electron density about the C--H bond. The electron density and thus the direction of the fluorination may be controlled by appropriate selection of substituent groupings in the substrate molecule.Novel 14α-fluorosteroids are also disclosed, including compounds having valuable androgenic or progestational activity and useful synthetic intermediates.
