Journal of the Chemical Society. Perkin transactions I p. 1169 - 1172 (1988)
Update date:2022-07-30
Topics:
Barbour, Robert H.
Robins, David J.
Reaction of 2,3-bis(hydroxymethyl)-1-methyl-2,5-dihydropyrrole<(+/-)-synthanecine A> (3) with thionyl chloride produces (+/-)-3-chloromethyl-2-hydroxymethyl-1-methyl-2,5-dihydropyrrolium chloride (11), which was treated with a series of anhydrides and base at room temperature to give the corresponding 6-monoesters of (+/-)-synthanecine A.Intramolecular nucleophilic substitution of the chlorine by carboxylate anion in the presence of base (DBU) gives the corresponding macrocyclic diesters of (+/-)-synthanecine A.The pyrrolizidine alkaloid analogues <(6), (7), and (16)-(20)> are prepared in better yields than using Corey-Nicolaou lactonisation conditions.A range of new 10-membered <(8)-(10) and (12)-(14)> and 11-membered <(15) and (21)> macrocyclic diesters of (+/-)-synthanecine A has been prepared.
View MoreFujian Wanke Pharmaceutical Co., LTD.
Contact:+86-598-5026002
Address:Economic development zone,jiangle county
NanJing Rate Biochemicals CO., LTD
Contact:+86-25-84931986
Address:NO. 1 Hongjing Road,Jiangning Science Park,Nanjing,China
Jiande City Silibase Silicone New Material Manufacture Co., Ltd.
Contact:15967177856
Address:Genglou Industrial Development Area
Contact:+86-515-88356562
Address:No.2, West Daqing Road, Yancheng, Jiangsu, China
Hangzhou Pharma & Chem Co.,Ltd.
Contact:+86-571-87040515
Address:No,139Qingchun Rd
Doi:10.1021/ol900362d
(2009)Doi:10.1007/BF00475659
(1987)Doi:10.1016/j.molliq.2017.07.055
(2017)Doi:10.1016/j.tet.2009.01.023
(2009)Doi:10.1021/ic802390c
(2009)Doi:10.1021/jo00242a051
(1988)
