5609. Lupinine
Nomenclature
Description and references
Naturally occurring l-form isolated from seeds and herb of Lupinus luteus L. and other L. species, Leguminosae also found in Anabasis aphylla L., Chenopodiaceae. Extraction procedure: J. F. Couch, J. Am. Chem. Soc. 56, 2434 (1934). Structure and synthesis: R. W. Willsttter, E. Fourneau, Ber. 35, 1910 (1902); P. Karrer et al., Helv. Chim. Acta 11, 1062 (1928); K. Winterfeld, F. W. Holschneider, Ber. 64B, 137, 692 (1931); K. Winterfeld, ibid. 692. Synthesis of racemic lupinine: F. W. Holschneider, K. Winterfeld, Arch. Pharm. 277, 192 (1939); G. C. Gerrans et al., Tetrahedron Lett. 1975, 4171; T. Iwashita et al., J. Org. Chem. 47, 230 (1982). Synthesis of racemic lupinine and epi-lupinine: G. R. Clemo et al., J. Chem. Soc. 1937, 965; H. Takahata et al., Chem. Pharm. Bull. 34, 4523 (1986); of l-epi-lupinine: M. L. Bremmer, S. M. Weinreb, Tetrahedron Lett. 24, 261 (1983). Absolute configuration of ()-form: R. C. Cookson, Chem. Ind. (London) 1953, 339. Crystal structure: A. Koziol et al., Acta Crystallogr. B34, 3491 (1978). Biosynthesis: Soucek, Schutte, Angew. Chem. 74, 901 (1962); W. M. Golebiewski, I. D. Spenser, J. Am. Chem. Soc. 106, 1441 (1984).
