Synthesis p. 1243 - 1245 (1997)
Update date:2022-08-02
Topics: Piperidines Expeditious synthesis Nitrone
Degiorgis
Lombardo
Trombini
The synthetic versatility of tetrahydrofuro[2,3-d]isoxazol-5(2H)ones, obtained from TMSOTf-promoted addition of 2-trimethylsilyloxyfuran to nitrones, is demonstrated in a two-step reductive sequence to give the title compounds. The cycloadducts obtained from a glycolaldehyde derived nitrone are first reduced with DIBAH, then hydrogenolyzed in the presence of Pd(OH)2 to give polyhydroxylated piperidines, including rac-fagomine. Direct hydrogenolysis of the same cycloadducts gives an easy entry to polyhydroxylated lactams.
View MoreContact:+86-27-67841589
Address:Add: 999 Gaoxin Road, Donghu New Technology Development Zone, Wuhan City, Hubei, China
Contact:+86-18653358619
Address:zibo
NINGBO PANGS CHEM INT’L CO.,LTD.
Contact:+86-574-27666845
Address:FLOOR 21,BUILDING NO.11,XIN TIAN DI,NO.689 SHI JI ROAD,NINGBO CHINA
Shanghai Mio Chemical Co., Ltd
Contact:0086 21- 64401188-622
Address:16 Floor NO.2 Jiefang Building, No. 4855 Dushi Road, 201100 Shanghai, P.R.China
Shanghai Forever Biotech Co., Ltd.
Contact:+86-21-69734790
Address:Room 5017/5019、5022、5024 of Technology Innovation Centre, No.1155, Gongyuan East Rd, QingPu District, Shanghai China.
Doi:10.1021/jo01062a002
(1961)Doi:10.1021/jm010382z
(2002)Doi:10.1016/S0223-5234(97)84014-7
(1997)Doi:10.1246/bcsj.46.194
(1973)Doi:10.1016/j.bmc.2019.07.015
(2019)Doi:10.1021/ol027352q
(2003)