Journal of the Chemical Society. Perkin transactions I p. 2049 - 2054 (1981)
Update date:2022-08-02
Topics:
Howard, Colin
Newton, Roger F.
Reynolds, Derek P.
Roberts, Stanley M.
Peracetic acid oxidation at -78 deg C of the dihydroxybicyclo<3.2.0>hepten-6-one (23) afforded the dihydroxylactone (24) which was protected as its bisdimethyl-t-butylsilyl ether (26) and reduced to the corresponding lactol (27).A Wittig reaction on (27), carried out in benzene with a short reaction time, gave mainly the required 11α-silyl ether (28) together with a trace of the 9α-silyl ether (29) which results from 1,5-migration of the silyl group.Oxidation of (28) followed by quantitative deprotection using aqueous HF in acetonitrile afforded (+/-)-PGE2 methyl ester (20).This short stereo- and regioselective total synthesis proceeds in an overall yield of 10percent starting from cyclopentadiene.
View Moreshanghai Tauto Biotech Co., Ltd
website:http://www.tautobiotech.com/en/index.htm
Contact:+86-21-51320588 ext. 8025
Address:No. 326, Aidisheng Rd , Zhangjiang Hi-tech Park, Shanghai , P.R.CHINA
Nanjing Chemipioneer Pharma&Tech Co.,Ltd
website:http://www.chemipioneer.com.cn
Contact:+86-25-52685700
Address:Room 305，A Block，Biological-Medicine Building，Business Start-up Center，Xin-ke 1st Road, High-tech development zone，Nanjing city，Jiangsu Province, China
website:http://www.simagchem.com
Contact:+86-592-2680277
Address:21/F Hualong Office Building,No.6 Hubin East Road, Xiamen,China
Contact:+86-577-65618087-605
Address:Room 402, Unit 4 Xinhu Bldg. Waitan Ruian City, Zhejiang China.
Dongtai Xinyuan Chemical Co., Ltd.
Contact:+86-21-56733000
Address:404F, 99Nong No.117 Zhongtan Rd. Shanghai
Doi:10.1021/om200093q
(2011)Doi:10.1039/b517728f
(2006)Doi:10.1021/ja0487877
(2004)Doi:10.1080/14756366.2020.1864630
(2021)Doi:10.1016/j.tet.2006.06.100
(2006)Doi:10.1021/jm060732n
(2006)
