专利号:US-4110380-A 优先权日:1974-05-06 标题 :Asymmetric synthesis of organic compounds 发明人:HAJOS ZOLTAN GEORGE; PARRISH DAVID RICHARD 权利人:HOFFMANN LA ROCHE 摘要:Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a 'meso' type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.
专利号:US-3962291-A 优先权日:1974-09-05 标 题:Total synthesis of 11-alkyl steroids 发明人:GARLAND ROBERT B; PAPPO RAPHAEL 权利人:SEARLE & CO 摘要:A novel total synthesis of 11-alkyl steroids, utilizing readily available and inexpensive raw materials, is described. The resulting products are useful and novel pharmacological agents possessing, for example, selective hormonal properties.
专利号:US-4045452-A 优先权日:1974-03-13 标题 :Steroid total synthesis process utilizing a cyanoalkyl A-ring precursor 发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL 权利人:HOFFMANN LA ROCHE 摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as wasl heretofore found necessary in previous steroid total synthesis processes.
专利号:US-4105676-A 优先权日:1975-12-22 标题 :Steroid total synthesis process utilizing a cyanoalkyl a-ring precursor 发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL 权利人:HOFFMANN LA ROCHE 摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.
专利号:US-3965138-A 优先权日:1974-03-13 标 题:Steroid total synthesis process utilizing a cyanoalkyl A-ring precursor 发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL 权利人:HOFFMANN LA ROCHE 摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents γ-butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normally labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.
专利号:US-3898265-A 优先权日:1970-08-26 标 题 :Steriod total synthesis process utilizing a cyanoalkyl A-ring precursor 发明人:COHEN NOAL; ROSENBERGER MICHAEL; SAUCY GABRIEL 权利人:HOFFMANN LA ROCHE 摘要:A multi-step, stereospecific total synthesis of steroids utilizing intermediates having a cyanoalkyl A-ring precursor is disclosed. The initial starting materials for this process are the relatively inexpensive and commercially available reagents gamma -butyrolactone and sodium cyanide. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly 19-norsteroids. It is a feature of this process that conditions employed during the multiple step synthesis are selected so as to retain the normaly labile nitrile group even during hydrogenation and hydrolysis steps. In this manner, it is possible to employ the nitrile group as an A-ring precursor without resorting to protective groups as was heretofore found necessary in previous steroid total synthesis processes.
[参考文献]: Victor J. Grenda, Et Al. A Convenient Synthesis Of 2-Methylcyclopentane-1,3-Dione. Return To Issueprevarticlenext [参考文献]: Bryson W Katona, Et Al. Enantiomeric Deoxycholic Acid: Total Synthesis, Characterization, And Preliminary Toxicity Toward Colon Cancer Cell Lines. J Org Chem. 2007 Nov 23;72(24):9298-307. [参考文献]: Randy M Wadkins, Et Al. Identification And Characterization Of Novel Benzil (Diphenylethane-1,2-Dione) Analogues As Inhibitors Of Mammalian Carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15.
合成参考文献
摘要:Wang, X.-W.; Wang, Y.; Jia, J., Science of Synthesis: Asymmetric Organocatalysis, (2012) 1, 2. 摘要:Hu, X.; Maimone, T. J., Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (2015) 1, 174. 摘要:Itsuno, S.; Ullah, M. S., Science of Synthesis: Flow Chemistry in Organic Synthesis, (2018) 1, 367. 摘要:Logeswaran, R.; Aravindan, N.; Jeganmohan, M., Science of Synthesis: Cross-Dehydrogenative Coupling, (2023) nan, 30.