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 MoreJIAXING SUNS INTERNATIONAL TRADE CO LTD
Contact:18367306858
Address:No.123,Huixin Avenue,Huimin Dist
Shanghai Dynamic Industrial Co.,Ltd.
website:http://www.shdynamic.com
Contact:86-021 3392 6680
Address:Room 805 Information Tower, No.1403 Minsheng Road, Pudong New Area, Shanghai 200135, P. R. China
Contact:+86-574-89075960
Address:#100 Xiang Yun Road, New High tech area, Ningbo, China
Contact:+852-8198 2399
Address:9E, Leapont Industrial Building, 18-28 Wo Liu Hang Road, Shatin, New Territories, Hong Kong
Contact:+86-571-28186845
Address:Room 1224,Eastcom Mansion,398 Wensan Road,Hangzhou,310013 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)