A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide

Lee J. Silverberg; Sean Kelly; Purushotham Vemishetti; David H. Vipond; Frank S. Gibson; Brian Harrison; Richard Spector; John L. Dillon

doi:10.1021/ol006262n

A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide

Lee J. Silverberg, Sean Kelly, Purushotham Vemishetti, David H. Vipond, Frank S. Gibson, Brian Harrison, Richard Spector, John L. Dillon

Penn State Schuylkill

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

(formula presented) 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.

Original language	English (US)
Pages (from-to)	3281-3283
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	21
DOIs	https://doi.org/10.1021/ol006262n
State	Published - Oct 19 2000

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol006262n

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title = "A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide",

abstract = "(formula presented) 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.",

author = "Silverberg, {Lee J.} and Sean Kelly and Purushotham Vemishetti and Vipond, {David H.} and Gibson, {Frank S.} and Brian Harrison and Richard Spector and Dillon, {John L.}",

year = "2000",

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language = "English (US)",

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T1 - A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide

AU - Silverberg, Lee J.

AU - Kelly, Sean

AU - Vemishetti, Purushotham

AU - Vipond, David H.

AU - Gibson, Frank S.

AU - Harrison, Brian

AU - Spector, Richard

AU - Dillon, John L.

PY - 2000/10/19

Y1 - 2000/10/19

N2 - (formula presented) 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.

AB - (formula presented) 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.

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U2 - 10.1021/ol006262n

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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

A crystallization-induced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide

Abstract

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