A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide.
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.
Silverberg
L J
LJ
Bristol-Myers Squibb Co., Technical Operations Development, Chemical Development Laboratories, P.O. Box 4755, Syracuse, New York 13221-4755, USA.
Kelly
S
S
Vemishetti
P
P
Vipond
D H
DH
Gibson
F S
FS
Harrison
B
B
Spector
R
R
Dillon
J L
JL
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D005047:Etoposide / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides; D005047:Etoposide