5906. Mesembrine
Nomenclature
Description and references
Alkaloid used in preparing Channa, a drug of Southwest Africa. Occurs naturally as the ()-form. From Sceletium expansum L., S. tortuosum L., Aizoaceae: Hartwick, Zwicky, Apoth. Ztg. 29, 925 (1914); Rimington et al., J. Vet. Sci. Animal Ind. 9, 187 (1938), C.A. 32, 42799 (1938). Structure: Popelak et al., Naturwissenschaften 47, 156 (1960). Configuration: P. W. Jeffs et al., J. Am. Chem. Soc. 91, 3831 (1969). Synthesis of (±) form: Shamma, Rodriguez, Tetrahedron Lett. 1965, 4847; O. Hoshino et al., Heterocycles 10, 61 (1978); of (±)-form and trans isomer: Oh-Ishi, Kugita, Chem. Pharm. Bull. 18, 299 (1970). Synthesis of (+)-form: Yamada, Otani, Tetrahedron Lett. 1971, 1133; eidem, Chem. Pharm. Bull. 21, 2130 (1973). Stereoselective synthesis of (±)-form: Wijnberg, Speckamp, Tetrahedron Lett. 1975, 3963; eidem, Tetrahedron 34, 2579 (1978); S. F. Martin et al., J. Org. Chem. 44, 3391 (1979); S. Takano et al., Chem. Lett. 1981, 1385. Enantioselective synthesis of natural mesembrine: eidem, Tetrahedron Lett. 22, 4479 (1981). Biosynthesis: Jeffs et al., J. Am. Chem. Soc. 93, 3752 (1971); eidem, Chem. Commun. 1977, 60. Review of mesembrine alkaloids: A. Popelak, G. Lettenbauer in The Alkaloids vol. IX, R. H. F. Manske, Ed. (Academic Press, New York, 1967) pp 467-481; R. V. Stevens in The Total Synthesis of Natural Products vol. 3, J. ApSimon, Ed. (Wiley, New York, 1977) pp 443-453.
