(8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene

(8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  An oily alkaloid isolated from various species of Ormosia, this hex acyclic base has [α]₅₈₉ -11°C and [α]₄₃₆ - 21.3 . It may be characterized as the perchlorate, colourless prisms from MeOH-Et20, m.p. 23S-7°C; the picrate, light yellow needles from Me2CO-Et20, m.p. 237°C (dec.) and the N-methyl derivative, m.p. 103°C which has [α]₅₈₉ + 5° and [α]₄₃₆+ 19° and gives a methiodide, m.p. 209-211°C. Two of the nitrogen atoms are tertiary, the third being present as an imino group. The original structure has been revised to make the alkaloid the 11-epimer of ormosinine (q.v.).

• Einzelnachweise

  Lloyd, Horning.,J. Amer. Chem. Soc., 80, 1506 (1958)
  Naegeli, Wildman, Lloyd., Tetrahedron Lett., 2069,2075 (1963)
  Deslongchamps, Wilson, Valenta., ibid, 3896 (1964)
  Revised structure:
  Wilson., Chem. Ind., 472 (1965)
  Wilson., Tetrahedron, 21, 2561 (1965)
  Crystal structure:
  Karle, Karle., Tetrahedron Lett., 1659 (1966)