Journal of Organic Chemistry p. 2594 - 2599 (1984)
Update date:2022-08-03
Topics: Synthetic studies Total synthesis DL-Validoxylamines A and B Validamycines
Ogawa, Seiichiro
Ogawa, Takao
Iwasawa Yoshikazu
Toyokuni, Tatsushi
Chida, Noritaka
Suami, Testsuo
The first synthesis of racemic validoxylamine A (3) and B (4), constituents of antibiotic validamycins, is described.For construction of these types of pseudodisaccharides containing an imino linkage, a coupling reaction of the protected anhydro derivative of DL-pentahydroxy(hydroxymethyl)cyclohexane (5) with the DL-trihydroxy(hydroxymethyl)cyclohexylamine or -cyclohexenylamine (6 or 7) was untertaken.All possible diastereoisomers (four pairs of enantiomeres) formed by the reaction of 5 with 6, employed for synthesis of 4, could be separated by chromatography on silica gel, and the relative configuration in two of the enantiomeric pairs, deduced on the basis of 1H-NMR spectroscopy, were confirmed by identification of one pair with an authentic chiral sample 4.On the other hand, the intermediate enantiomeric pair 13a obtained by a coupling of the appropriate epoxide 5 and amine 7 underwent mainly dehydration with sulfuryl chloride in pyridine to give the pair of enantiomers 19a, one of which was the protected derivative of 3.In contrast, the diastereomeric pair of enantiomers 13b yielded selectively the chloride 18b, which was then transformed into the enantiomeric pair 21b by dehydrochlorination followed by deprotection.
View MoreNINGBO 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 Sungo Technology Chemical Co., Ltd
Contact:0086-21-51385579
Address:Room2010, F/20, Tonghua Plaza, NO 345 Jinxiang Road, Jinqiao Export Processing Zone, Shanghai, 201206 P.R.CHINA
Tianjin Jingye Fine Chemicals Co., Ltd.
Contact:+86-15722078107; +86-22-26911407
Address:Bohua Fine Chemicals Base of Petrochemical Industry Park, Nanhuan Road, Dagang District, Tianjin, 300271, P. R. China
Jinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
Chemvon Biotechnology Co. Ltd.
website:http://www.chemvon.com
Contact:86-21-58550039;86-21-31268550-8004
Address:Suite B-10#, 6999 Chuansha Road, Pudong District, Shanghai 201202, China
Doi:10.1021/jo060545x
(2006)Doi:10.1016/j.carres.2020.108080
(2020)Doi:10.1021/ja01642a039
(1954)Doi:10.1021/jo302795w
(2013)Doi:10.1007/BF00513870
(1984)Doi:10.1016/j.tet.2006.06.021
(2006)