Stereocontrolled synthesis of the northern part of potent proteasome inhibitor TMC-95A.

Inoue, M; Furuyama, H; Sakazaki, H; Hirama, M

Inoue, M; Furuyama, H; Sakazaki, H; Hirama, M.

Afiliación

Inoue M; Department of Chemistry, Graduate School of Science, Tohoku University, and CREST, Japan Science and Technology Corporation (JST), Sendai 980-8578, Japan.

Org Lett ; 3(18): 2863-5, 2001 Sep 06.

Article en En | MEDLINE | ID: mdl-11529776

RESUMEN

[reaction: see text]. A protected version of the northern part of TMC-95A, a potent and selective proteasome inhibitor, was synthesized with full stereochemical control. Highlights of this synthesis include (i) a (Z)-selective Mizoroki-Heck reaction to construct the oxyindole portion, (ii) a diastereoselective epoxidation, (iii) a 6-endo selective epoxide opening by Boc carbonyl group to establish the stereochemistry of C6, and (iv) a 1,3-elimination reaction of the L-allo-threonine derivative under Mitsunobu conditions to afford the (Z)-1-propenylamine.

Asunto(s)

Péptidos Cíclicos/síntesis química; Inhibidores de Proteasas/síntesis química; Cisteína Endopeptidasas; Conformación Molecular; Complejos Multienzimáticos/antagonistas & inhibidores; Péptidos Cíclicos/química; Péptidos Cíclicos/farmacología; Inhibidores de Proteasas/química; Inhibidores de Proteasas/farmacología; Complejo de la Endopetidasa Proteasomal

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos Cíclicos / Inhibidores de Proteasas Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2001 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

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