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 MoreContact:+86-579-85206992
Address:No 451 chouzhou north road ,room 1106 int'l business center , yiwu ,china
Contact:+86-20-32051076
Address:1105,Building A, International Business Incubator,Science City
Nanjing Vincero International Trading Co.,Ltd
Contact:8618936897229
Address:NO.68, ZhuShan Road, JiangNing WanDa Plaza, Building E Room 1703
SHIJIAZHUANG HENRYTE CHEMICALS CO,.LTD(expird)
Contact:+86-311-85208698 311-80837698
Address:NO.166, yuhua west road, SHIJIAZHUANG, China
Jiaxing Trustworthy Import And Export Co.,Ltd
Contact:+86-573-82030555
Address:Room 1202, Unit B, Charming plaza,No.1558 East Zhongshan Road , Jiaxing City, Zhejiang 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)
