Title: Hasubanonine
CAS Registry Number: 1805-85-2
CAS Name: 7,8-Didehydro-3,4,7,8-tetramethoxy-17-methylhasubanan-6-one
Molecular Formula: C21H27NO5
Molecular Weight: 373.44
Percent Composition: C 67.54%, H 7.29%, N 3.75%, O 21.42%
Literature References: Alkaloid having a modified morphinan skeleton with a five membered heterocyclic ring, hitherto unknown in natural sources. (Alkaloids with this unique skeleton are called hasubanan alkaloids; see S. Shiotani, T. Kometani, Tetrahedron Lett. 1976, 767 for synthesis of hasubanan skeleton). Isolated from Stephania japonica Miers, Menispermaceae: Kondo et al., Annu. Rep. Itsuu Lab. 2, 35 (1951); Satomi, ibid. 3, 37 (1953); Kondo, Satomi, ibid. 8, 41 (1957); C.A. 47, 5951f (1953); 48, 2728c (1954); 51, 17956i (1957). Structure: Tomita et al., Tetrahedron Lett. 1964, 2937; eidem, Chem. Pharm. Bull. 13, 538 (1965). Total synthesis: Ibuka et al., Tetrahedron Lett. 1970, 4811; Chem. Pharm. Bull. 22, 782 (1974). Biosynthesis: A. R. Battersby et al., Chem. Commun. 1974, 773; eidem, J. Chem. Soc. Perkin Trans. 1 1981, 2010, 2016, 2030. Review: Y. Inubushi, T. Ibuka in The Alkaloids vol. XVI, R. H. F. Manske, Ed. (Academic Press, New York, 1977) pp 393-428.
Properties: Prisms from methanol, mp 116°. [a]D -219° (ethanol).
Melting point: mp 116°
Optical Rotation: [a]D -219° (ethanol) |