Oxidation of aconitine by potassium permanganate. A new N-de-ethyl-7,17-secoimino derivative
The alkaloid aconitine was oxidized by potassium permanganate in aqueous acetone. It was shown that the oxidation formed three products including the previously described N-de-ethylaconitine, N-de-ethyl-19-oxoaconitine, and a new N-de-ethyl-7,17-secoimino
DEOXYGENATION REACTIONS OF C19-DITERPENOID ALKALOIDS
Efficient methods for deoxygenation of secondary and tertiary alcohols of some C19-diterpenoid alkaloids are presented.Delphisine (12) was converted to 1-deoxydelphisine (19) via either 1,2-pyrodelphisine (17) or phenyl thionocarbonate 20.The following alkaloids were deoxygenated via their thiocarbonylimidazolyl derivatives: 14-acetyldelcosine (13) to 14-acetyl-1-deoxydelcosine (22); alkaline hydrolysis of 22 gave 1-deoxydelcosine (23); aconitine (24) to 3-deoxyaconitine (27); yunaconitine (25) to crassicauline A (28).Deoxygenation of 14-acetyldictyocarpine (30) via the chloro-derivate 31 gave 14-acetyl-10-deoxydictiocarpine (34).Reduction of 31 with LiAlH4 gave the unusual elimination product 32.An improved partial synthesis of hypaconitine (35) from aconitine (24) is also presented.
Kulanthaivel, Palaniappan,Pelletier, S. William
p. 4313 - 4320
(2007/10/02)
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