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6900-87-4

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Studies on Aconitum species. XV. Deoxygenation reaction of aconitine type alkaloids
Mesaconitine (1) in tetrahydrofuran reacted with sodium hydride, a catalytic amount of imidazole, carbon disulfide and methyl iodide at room temperature to give the di-O-(S-methyl)thiocarbonate (5). The reductive cleavage of 5 with tri-n-butyltin hydride
Mori,Murayama,Bando,Kawahara
p. 2803 - 2806
(2007/10/02)

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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Chemical Properties

Melting Point: 197～198℃
Boiling Point: 671.3oC at 760 mmHg
Flash Point:359.8oC
Density: 1.35g/cm3
Vapor Pressure: 6.18E-19mmHg at 25°C
PKA: 12.21±0.70(Predicted)
PSA: 133.22000
LogP: 1.22510

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