Tetrahedron Asymmetry p. 935 - 948 (1997)
Update date:2022-08-04
Topics:
Amat, Mercedes
Coll, M.-Dolors
Bosch, Joan
Espinosa, Enric
Molins, Elies
Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of 1-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally Smith indolization. Whereas 2-(4-piperidylmethyl)indole 6 could not be converted to tetracyclic ABDE substructures of Strychnas alkaloids, photocyclization of chloroacetamide 14, derived from (piperidylmethyl)indole 13, satisfactorily afforded the stemmadenine-type tetracycle 15, which was then converted to the alkaloids (-)-tubifoline, (-)-tubifolidine, and (-19,20-dihydroakuammicine.
View MoreContact:+86 21 5017 5386
Address:No 999,Jiangyue Rd, Minhang Dist ,201114,Shanghai ,China
Xi'an Tizan Tech & Industry Co., Ltd.
Contact:86-18629066522
Address:C3009 TANG FENG INTERNATIONAL PLAZA, NO.18 FENGHUI NAN ROAD, XI'AN HIGH TECH ZONE, 710075 CHINA.
Suqian Ruixing Chemical Co., Ltd.
Contact:+86-527-80805666(总机);84836008(销售)
Address:3 Jingsilu, Zone north, Hubin Xincheng Development Park, Suqian, China
website:http://www.finerchem.com
Contact:+86-531-88989536
Address:New Material Industry Park, Jinan Ciyt, China
NINGBO YINZHOU PRECISE COLOR CO.,LTD.
Contact:86-574-88139809 86-574-83033159
Address:Qiming Road,Yinzhou,Ningbo,China
Doi:10.1039/b105116b
(2001)Doi:10.1016/j.bmc.2019.115141
(2019)Doi:10.1039/P29830000049
(1983)Doi:10.1002/hlca.19900730415
(1990)Doi:10.1016/0960-894X(96)00451-9
(1996)Doi:10.1021/jo961527q
(1996)