3907-67-3Relevant academic research and scientific papers
A novel strategy for the enantioselective synthesis of the steroidal framework using cascade ring expansion reactions of small ring systems- asymmetric total synthesis of (+)-equilenin
Nemoto, Hideo,Yoshida, Masahiro,Fukumoto, Keiichiro,Ihara, Masataka
, p. 907 - 910 (1999)
Enantioselective synthesis of (+)-equilenin (1) utilizing a novel strategy is described. The key steps are two cascade ring expansion reactions of small ring systems; 1) chiral (salen)Mn(III) complex-catalyzed cascade reaction of cyclopropylidene; 2) Pd(II)-mediated cascade reaction of the cyclobutanol.
Asymmetric total synthesis of (+)-equilenin utilizing two types of cascade ring expansion reactions of small ring systems
Yoshida, Masahiro,Ismail, Mohamed Abdel-Hamid,Nemoto, Hideo,Ihara, Masataka
, p. 2629 - 2635 (2000)
Enantioselective synthesis of (+)-equilenin 1 utilizing two types of cascade ring expansion reactions of small ring systems is described.The first key step is an asymmetric epoxidation-ring expansion reaction of cyclopropylidene derivatives to afford chiral cyclobutanones. We found that both the fructose-derived chiral ketone and the chiral (salen)Mn(III) complex were effective catalysts for the asymmetric induction. The second key step is the palladium-promoted cascade ring expansion-intramolecular insertion reaction of the isopropenylcyclobutanol. Solvents were an important factor for the diastereoselective formation of hydrindanes. By utilizing these methodologies, the asymmetric total synthesis of (+)-equilenin 1 has been accomplished. The Royal Society of Chemistry 2000.
Synthesis and study of equilenin derivatives and modified analogs
Urusova,Gluzdikov,Selivanov,Starova,Nikolaev,Shavva
, p. 506 - 512 (2004)
Modified equilenin analogs were synthesized with a view to examine the relation between the structure and biological properties of steroid estrogens. The 1H and 13C NMR signals of six estra-1,3,5,7,9- pentaenes were completely assigned using homo- and heteronuclear correlation NMR spectroscopy. The structure of equilenin methyl ester was determined by X-ray analysis. Among the synthesized steroids, compounds were found which exhibit hypocholesterinemic activity with no uterotropic and hypertriglyceridemic effects.
Practical semisynthesis of equilenin and its derivatives
Yue, Tao,Li, Hong-Ping,Ding, Kai
supporting information, p. 4850 - 4853 (2016/10/07)
Equilenin 2 and its derivatives are important intermediates in the synthesis of steroidal drugs. Until now, these estrogens were produced by extraction from pregnant mare's urine due to the lack of efficient synthetic methods. Most reported semisyntheses of equilenin involve expensive raw materials or toxic reagents to suppress undesired epimerization at C/D ring juncture. Herein, we reported a practical synthesis of highly pure equilenin and its derivatives from an easily available raw material 6 with conventional reagents.
Synthesis of A-ring aromatic steroids
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, (2008/06/13)
Total synthesis of steroids of the estrone and equilenin series involving conjugate 1,4-addition of a meta-substituted benzyl organometallic reagent to a C/D bicyclic methylene ketone. An aromatization of the B-ring of Δ 9(11) estrone derivatives.
