The Total Synthesis of AB3217-A, a Novel Anti-mite Substance, via Intermolecular Etherification and Intramolecular Glycosylation

Autor:	Kuniaki Tatsuta, Mitsuhiro Kinoshita, Tetsuro Tamai, Tadashi Kamio, Masaya Nakata
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Glycosylation chemistry Stereochemistry Intramolecular force Alkoxide Intermolecular force chemistry.chemical_element Total synthesis Stereoselectivity Lithium General Chemistry Pyrrolidine
Zdroj:	Bulletin of the Chemical Society of Japan. 67:3057-3066
ISSN:	1348-0634 0009-2673
Popis:	The first total synthesis of AB3217-A has been achieved. The deacetylanisomycin unit, (3S,4S,5R)-3-benzyloxy-1-(benzyloxycarbonyl)-5-[(1R)-1-hydroxy-1-(4-methoxyphenyl)methyl]-4-(2-tetrahydropyranyloxy)pyrrolidine (18), was prepared from dimethyl L-tartrate by a stereoselective pyrrolidine-ring formation and a stereoselective reduction of phenyl ketone as the key steps. The lithium alkoxide of 18 was coupled with the D-xylofuranose unit, phenyl 2,3-di-O-benzyl-5-O-trifluoromethanesulfonyl-1-thio-α-D-xylofuranoside which was prepared from 1,2 : 5,6-di-O-isopropylidene-α-D-glucofuranose, via an intermolecular etherificaiton. The resulting coupling product was subjected to de-O-tetrahydropyranylation and an intramolecular glycosylation to afford 4,12,13-tribenzyl-6-(benzyloxycarbonyl)AB3217-A (30). Final deprotection of 30 furnished AB3217-A.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9ffc907b0f2c835b496ae0dfe3d1f13d https://doi.org/10.1246/bcsj.67.3057 Zobrazit plný text záznamu