Studies on antihepatitic drugs. Total synthesis of (+/-)schizandrin C and its analogs.
This paper reports the total synthesis of (+/-) schizandrin, C, namely 5,6,7,8-tetrahydro-1, 12-dimethoxy-2, 3, 10, 11-bismethylenedioxy-6, 7-cis-dimethyldibenzo (a, c) cyclooctene (12B), a new active SGPT lowering principle isolated from the Chinese medical plant Schizandra chinensis, and its 6, 7-trans-dimethyl isomer (16B). We also synthesized two more isomers, namely 5, 6, 7, 8-tetrahydro-3, 10-dimethoxy-1, 2, 11, 12-bismethylenedioxy-6, and 7-cis-(and trans-) dimethyldibenzo (a, c) cyclooctene (12A and 16A). The NMR, UV and mass spectra of these four isomers are discussed. IR (in chloroform), UV, NMR and MS of synthetic schizandrin C (12B) are identical with those of the natural compound.
D000818:Animals; D034242:Cyclooctanes; D006505:Hepatitis / Q000188:drug therapy*; D006801:Humans; D017705:Lignans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010946:Plants, Medicinal; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet
D034242:Cyclooctanes; D017705:Lignans; D011083:Polycyclic Compounds; C031409:schizandrin C