3907-67-3Relevant articles and documents
Stereochemistry of steroid containing aromatic A-ring. I. Reaction of 9(11)-dehydroestrone.
Tsuda,Nozoe,Okada
, p. 1022 - 1027 (1963)
-
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.
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.
