(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
This furanoquinoline alkaloid has been obtained from the bark of the Australian
tree Flindersia ifflaiana. It is obtained in the form of a colourless gum which
cannot be crystallized. The alkaloid is laevorotatory with [α]
29D~~9 - 0.6° or
[α]
29D~~o - 3.6° (c 8.0, MeOH). From aqueous solvents, a crystalline hydrate is
formed, m.p. 62-3°C. The ultraviolet spectrum in MeOH shows absorption
maxima at 215, 236, 309 and 320 mil with a shoulder at 251 and an inflexion at
298 mil. A yellow crystalline picrate is known, m.p. 207-9°C. The probable
structure obtained from infrared and NMR spectra, and dependent upon analogy with other alkaloids of this type, has been confirmed by the total synthesis of
the (±)-form, m.p. 128-9°C.
Einzelnachweise
Bosson et al., Austral. 1. Chem., 16, 480 (1963)
Total syn thesis:
Chamberlain, Grundon., Tetrahedron Lett., 3547 (1967)
(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one Upstream-Materialien And Downstream Produkte
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