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

24 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",

month = oct,

day = "19",

doi = "10.1021/ol006262n",

language = "English (US)",

volume = "2",

pages = "3281--3283",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

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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.

UR - https://www.scopus.com/pages/publications/0034687183

UR - https://www.scopus.com/pages/publications/0034687183#tab=citedBy

U2 - 10.1021/ol006262n

DO - 10.1021/ol006262n

M3 - Article

C2 - 11029190

AN - SCOPUS:0034687183

SN - 1523-7060

VL - 2

SP - 3281

EP - 3283

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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