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

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3281-3283

  Silverberg, Lee J ^c   Kelly, Sean ^b   Vemishetti, Purushotham ^a   Vipond, David H ^b   Gibson, Frank S ^a   Harrison, Brian ^b   Spector, Richard ^a   Dillon, John L ^a,d  

^a BRISTOL MYERS SQUIBB COMPANY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

^c Johnson Matthey   (United States)

^d HONEYWELL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ETOPOSIDE; GLYCOSIDE;

ARTICLE; CHEMISTRY; CRYSTALLIZATION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CRYSTALLIZATION; ETOPOSIDE; GLYCOSIDES; STEREOISOMERISM;

EID: 0034687183     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006262n     Document Type: Article

References (40)

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35. Formation of the α-isomer with respect to the O-C bond of the sugar and lignan nucleus in coupled product 2 is not observed presumably due to steric hindrance of the α-face by the pendant aryl ring system.
36. 3 that were occluded in the crystals. Also, by quenching and workup, 2β can be isolated from acetonitrile at higher temperature (0 °C), allowing for a nearly complete purge of the 2α isomer.
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38. 3 as a reducing agent to the mixture following hydrogenation to maintain the reduced compound 5 that purges during crystallization. (Formula Presented)
39. For a synthesis of etoposide using 1-β-OTMS-4,6-O-ethylidene-glucose with an overall yield of 70%, see ref 2s.
40. Compound 4 can be prepared in greater than 90% of the β-isomer by heating the anomeric mixture below its melting point, see ref 4. Compound 4β will undergo anomerization under the reaction conditions, but at a slower rate than the coupling itself.