title: A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide.
abstract: The anticancer drug etoposide, 1, is prepared in 79% overall yield from readily available 4'-demethyl-4-epipodophyllotoxin, 3, and 4, 6-O-ethylidene-2,3-O-dibenzyl-D-glucose, 4, via a crystallization-induced stereoselective glycosidation reaction followed by catalytic hydrogenation.
authors.affiliation: Bristol-Myers Squibb Co., Technical Operations Development, Chemical Development Laboratories, P.O. Box 4755, Syracuse, New York 13221-4755, USA.
authors.forename: L J
authors.initials: LJ
authors.lastname: Silverberg
authors.forename: S
authors.initials: S
authors.lastname: Kelly
authors.forename: P
authors.initials: P
authors.lastname: Vemishetti
authors.forename: D H
authors.initials: DH
authors.lastname: Vipond
authors.forename: F S
authors.initials: FS
authors.lastname: Gibson
authors.forename: B
authors.initials: B
authors.lastname: Harrison
authors.forename: R
authors.initials: R
authors.lastname: Spector
authors.forename: J L
authors.initials: JL
authors.lastname: Dillon
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D005047:Etoposide / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides; D005047:Etoposide