Tetrahedron p. 4989 - 4998 (1988)
Update date:2022-08-05
Topics:
Achmatowicz, B.
Baranowska, E.
Daniewski, A. R.
Pankowski, J.
Wicha, J.
A new method for stereospecific construction of the allylic alcohol moiety of prostaglandins, based on application of optically active α-hydroxy aldehydes, is described.In the presence of BF3*Et2O, lithiated sulphones 1 prepared from Corey aldehyde, and carbonyl compounds 2 give the corresponding adducts 3 in moderate to excellent yields, while in the absence of the Lewis acid either no products or only their traces were formed.The addition products 3, in the form of benzoates, mesylates or free alcohols, were subjected to reductive elimination by means of sodium amalgam to give the alkenes 4.Compounds 4d and 4f were transformed into racemic and natural PGF2α, respectively, in line with the known method.
View MoreXi'an Unique Electronic and Chemical Co., Ltd.
Contact:+86-029-88238008
Address:1703# B BUILDING WEST ELECTRONIC ZONE, XI'AN, CHINA
Lianyungang Ningkang Chemical Co., Ltd
Contact:.+86-518-88588008
Address:http://www.chemnk.com
Contact:86-379-63338609
Address:Jiudian Village,Deting Town,Song County,Luoyang
Contact:+86-731-84427351
Address:154 JIANXIANG SOUTH ROAD
Shenyang Mole pharmaceutical Technology Development Co.,Ltd
Contact:+86-24-31204918/13889278616
Address:No.44, wanliutang road, shenhe District of Shenyang
Doi:10.1021/om00095a006
(1988)Doi:10.1016/S0960-894X(03)00393-7
(2003)Doi:10.1016/j.ejmech.2016.04.017
(2016)Doi:10.1021/ol802794t
(2009)Doi:10.1016/S0040-4039(01)91161-X
(1984)Doi:10.1021/jm034015u
(2003)
