Tetrahedron p. 4313 - 4320 (1988)
Update date:2022-09-26
Topics:
Kulanthaivel, Palaniappan
Pelletier, S. William
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.
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(1988)
