Journal of Organic Chemistry p. 3853 - 3857 (1990)
Update date:2022-07-30
Topics:
Barrett, Anthony G. M.
Lebold, Suzanne A.
The stereospecific total synthesis of polyoxin C and the nucleoside analogue, uracil polyoxin C, is described.Condensation of (phenylthio)nitromethane with methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 5 gave the (Z)-nitro olefin 6.Addition of potassium trimethylsilanoate and ozonolysis gave the α-hydroxy thioester 7, which was formed with excellent diastereoselectivity.The alcohol 7 was converted into polyoxin C (1) and uracil polyoxin C (2) via the azide 11 and base incorporation using the Vorbrueggen method.
View MoreContact:+86 512 6287 2180
Address:398 Ruoshui Road, Suzhou Industrial Park, Suzhou, Jiangsu, P. R. China
Shanghai Standard Biotech Co., Ltd.
Contact:+86-18502101150
Address:Room 103, Building 2nd, NO.720, Cailun Road , Pudong District, Shanghai, China
Shanghai Yuanding Chem. Sci. & Tech. Co., Ltd.
website:http://www.shydtec.com
Contact:86-21-57721279
Address:Science and Technology Park, Songjiang District, Shanghai, China
NanJing KaiHeng Chemical CO., LTD.
Contact:+86-25-85768391
Address:RM.1704, D, WANDA PLAZA, NO.110, MIDDLE JIANGDONG ROAD, NANJING, CHINA
Contact:(1) 206-3550089
Address:5115 NE 8TH PL, Renton, WA 98059 USA
Doi:10.1039/c39890000770
(1989)Doi:10.1016/0223-5234(89)90076-7
(1989)Doi:10.1021/ol200202g
(2011)Doi:10.1039/c8md00430g
(2018)Doi:10.1016/j.crci.2010.02.002
(2010)Doi:10.1007/s10973-011-2160-y
(2013)
