The bark of Pithecolobiurn sarnan Benth. yields this macro cyclic alkaloid, first
obtained by Greshoff who gave it the formula C17H360N 3 and [α]27D - 12.12°
(EtOH), yielding a dihydrochloride with [α]27D - 19.3° (H20). It has been stated
to yield methylamine and piperidine on distillation with Zn dust. A tripicrolonate is known as colourless, or pale yellow, crystals from MeOH-Me2CO, m.p.
134-5"C. The tetraacetate is a colourless oil.
Greshoff., Ber., 23,3541 (1890)
van ltallie.,Pharrn. Weekbl., 69,941 (1932)
Wiesneretal., Can. J. Chern., 30,761 (1952)
Wiesner et aI., J. Arner. Chern. Soc., 75,6348 (1953)
Orr, Wiesner., Chern. & Ind., 672 (1959)
Orr, Weisner., Tetrahedron Lett., No. 16, II (1960)
Structure:
Wiesner, MacDonald, Bankiewicz., Can. J. Chern., 46, 1881 (1968)
