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.
View MoreNanjing Zelang Medical Technology Co. Ltd
Contact:86-25-83063290/13770714480
Address:Ganjiabian 108# 01 Unit,701-702 room,Yao Hua Street,Qixia District,Nanjing,Jiangsu,China
KINHENG CHEMICAL(SHANGHAI)CO., LTD.
Contact:+8621-60490170
Address:Room401, No.28,Lane 189, Yangshupu Rd. Shanghai, China.
SHANDONG CREDAGRI CHEMICAL CO., LTD.
Contact:+86-531-88872050
Address:ROOM 601A, BUILDING 2, SHUNTAI SQUARE, NO. 2000 SHUNHUA ROAD, HI-TECH DEVELOPMENT ZONE, JINAN, CHINA.
Contact:410-273-7300; 800-221-3953
Address:4609 Richlynn Dr., PO Box 369, Belcamp, MD, 21017-0369, USA
Jiaozuo Zhongwen Trading Coporation Limited
Contact:--
Address:East Renmin Road
Doi:10.1039/b916506a
(2010)Doi:10.1016/j.tetlet.2012.05.129
(2012)Doi:10.1021/acs.organomet.0c00627
(2020)Doi:10.1016/j.bmcl.2009.12.035
(2010)Doi:10.1021/jo00366a011
(1986)Doi:10.1039/c39880001447
(1988)
