9082. Tazettine
Nomenclature
CAS number: 507-79-9
Sekisanine; sekisanoline; ungernine. C18H21NO5; mol wt 331.36.
C 65.24%, H 6.39%, N 4.23%, O 24.14%.
Description and references
From Narcissus tazetta L., Lycoris radiata Herb., Ungernia sewerzowi (Rgl.) Fedtsch., and other Amaryllidaceae: Spth, Kahovec, Ber. 67, 1501 (1934). Structure and stereochemistry: Ikeda et al., J. Chem. Soc. 1956, 4749. Abs config: Highet, Highet, Tetrahedron Lett. 1966, 4099. Synthesis: Hendrickson et al., J. Am. Chem. Soc. 92, 5538 (1970); Tsuda et al., Tetrahedron Lett. 1972, 3153. Biosynthesis: Fales, Wildman, J. Am. Chem. Soc. 86, 294 (1964). Identity with sekisanine and sekisanoline: Ikeda et al., loc. cit. Stereospecific total synthesis: Hendrickson et al., J. Am. Chem. Soc. 96, 7781 (1974); S. Danishefsky et al., ibid. 102, 2838 (1980); 104, 7591 (1982).
