Studies toward the synthesis of salinosporamide A, a potent proteasome inhibitor

被引：23

作者：

Caubert, Virginie ^{[1
]}

Langlois, Nicole ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 26期

关键词：

protease inhibitor; salinosporamide A; pyroglutamate; 1,3-dipolar cycloadditions; diazomethane; N-methylnitrone; samarium diiodide;

D O I：

10.1016/j.tetlet.2006.04.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An alpha-methylenepyrrolidinone bearing all the functionalities and relative configurations of an advanced intermediate in the synthesis of salinosporamide A and analogues has been synthesized front methyl pyroglutamate through regio- and stereoselective N-methylnitrone cycloaddition. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4473 / 4475

页数：3

共 27 条

[1] REACTIONS WITH DIAZOALKANES .1. ACTION OF DIAZOMETHANE ON N-PHENYLMALEIMIDE, WITH A SPECIAL NOTE ON PYROLYSIS PRODUCTS OF PYRAZOLINE [J].

AWAD, WI ;

ABDEL, SM ;

OMRAN, R ;

SOBHY, M .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (10) :4126-&

[2] A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity [J].

Corey, EJ ;

Li, WD ;

Reichard, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2330-2336

[3] Kinetic resolutions and enantioselective transformations of 5-(acyloxy)pyrrolinones using Candida antarctica lipase B:: Synthetic and structural aspects [J].

Cuiper, AD ;

Kouwijzer, MLCE ;

Grootenhuis, PDJ ;

Kellogg, RM ;

Feringa, BL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9529-9537

[4] Total synthesis of salinosporamide A [J].

Endo, A ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8298-8299

[5] Salinosporamide A:: A highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora [J].

Feling, RH ;

Buchanan, GO ;

Mincer, TJ ;

Kauffman, CA ;

Jensen, PR ;

Fenical, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (03) :355-+

[6] A BETA-LACTONE RELATED TO LACTACYSTIN INDUCES NEURITE OUTGROWTH IN A NEUROBLASTOMA CELL-LINE AND INHIBITS CELL-CYCLE PROGRESSION IN AN OSTEOSARCOMA CELL-LINE [J].

FENTEANY, G ;

STANDAERT, RF ;

REICHARD, GA ;

COREY, EJ ;

SCHREIBER, SL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (08) :3358-3362

[7]

HERMET JP, 2006, IN PRESS SYNTH COMMU, V36

[8] Reductive cleavage of N-O bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide [J].

Keck, GE ;

Wager, TT ;

McHardy, SF .

TETRAHEDRON, 1999, 55 (40) :11755-11772

[9] 1,3-DIPOLAR CYCLOADDITIONS OF NITRONES TO ALPHA,BETA-UNSATURATED GAMMA-LACTAMS DERIVED FROM (S)-PYROGLUTAMINOL [J].

LANGLOIS, N ;

VANBAC, N ;

DAHURON, N ;

DELCROIX, JM ;

DEYINE, A ;

GRIFFARTBRUNET, D ;

CHIARONI, A ;

RICHE, C .

TETRAHEDRON, 1995, 51 (12) :3571-3586

[10] Diastereoselective synthesis of (2S,3S,4S)-3-hydroxy-4-methylproline, a common constituent of several antifungal cyclopeptides [J].

Langlois, N ;

Rakotondradany, F .

TETRAHEDRON, 2000, 56 (16) :2437-2448

← 1 2 3 →