Journal of the American Chemical Society p. 2954 - 2961 (1984)
Update date:2022-07-29
Topics:
Narasaka, Koichi
Sakakura, Toshiyasu
Uchimaru, Tadafumi
Guedin-Vuong, Denis
A new esterification reaction has been developed utilizing a (methylthio)methyl (MTM) group as an activable protecting group of carbocyclic acid.A total synthesis of a 12-membered pyrrolizidine alkaloid, (+/-)-integerrimine (1), has been achieved by applying the above method to formation of the macrocyclic bislactone skeleton.The acid anhydride (16b) of the integerrinecic acid derivative was coupled with lithium alkoxide of retronecine silyl ether (5b) in the presence of DMAP to afford the α,β-unsaturated ester.Oxidation of the MTM group afforded an active (methylsulfonyl)methyl ester (28b), which cyclized to give the macrocyclic bislactone 29.
View MoreGuangxi Shanyun Biochemical Science and Technology Co., Ltd
Contact:+86-0772--6828887
Address:#2 Industrial Park of Luzhai County, Liuzhou, Guangxi, China
Contact:+86-18653358619
Address:zibo
Shanghai Harvest Chemical Ind. Co., Ltd.
Contact:021-51385350
Address:ROOM 806-807, AI LI CHEN BUILDING, No.333 JINGXIANG ROAD, PUDONG DISTRICT, 201206, SHANGHAI
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
Contact:+86-21-6856-1349 523-87676172
Address:No16 . BinJiang Road . Taixing Economy Developing Area .JiangSu Province . China
Doi:10.1055/s-2006-939698
(2006)Doi:10.1021/ja00868a046
(1962)Doi:10.1021/jo802446y
(2009)Doi:10.1021/jo00187a031
(1984)Doi:10.1021/jo00185a011
(1984)Doi:10.1016/0008-6215(83)88359-1
(1983)