Enantioselective construction of the oxidized tryptophan fragment of proteasome inhibitors TMC-95A and TMC-95B

被引：45

作者：

Ma, DW ^{[1
]}

Wu, QQ ^{[1
]}

机构：

[1] Acad Sinica, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 47期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0040-4039(00)01657-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidized tryptophan analogue 5, a proposed intermediate for a synthesis of the proteasome inhibitors TMC-95A and TMC-95B, is prepared using the condensation of oxindole 7 with the (R)-Garner aldehyde and stereoselective dihydroxylation of olefin 6 as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9089 / 9093

页数：5

共 14 条

[1]

ANGERMANN J, 1995, SYNLETT, P1014

[2] ASYMMETRIC DIHYDROXYLATION (AD) OF N,N-DIALKYL AND N-METHOXY-N-METHYL ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED AMIDES [J].

BENNANI, YL ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1993, 34 (13) :2079-2082

[3]

CHEIKH A B, 1988, Journal of Organic Chemistry, V53, P929

[4] A NEW EFFICIENT AND MILD SYNTHESIS OF 2-OXINDOLES BY ONE-POT WOLFF-KISHNER LIKE REDUCTION OF ISATIN DERIVATIVES [J].

CRESTINI, C ;

SALADINO, R .

SYNTHETIC COMMUNICATIONS, 1994, 24 (20) :2835-2841

[5] SUBSTITUTED OXINDOLES .5. SYNTHESIS AND STEREOCHEMISTRY OF SOME SUBSTITUTED 3-BENZYLIDENE-1-METHYLINDOL-2(3H)-ONES [J].

DAISLEY, RW ;

WALKER, J .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (20) :3357-&

[6] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[7] SYNTHESIS AND STRUCTURE ELUCIDATION OF A NOVEL ECDYSTEROID, GERARDIASTERONE [J].

HONDA, T ;

TAKADA, H ;

MIKI, S ;

TSUBUKI, M .

TETRAHEDRON LETTERS, 1993, 34 (51) :8275-8278

[8] TMC-95A, B, C, and D, novel proteasome inhibitors produced by Apiospora montagnei Sacc. TC 1093 -: Taxonomy, production, isolation, and biological activities [J].

Koguchi, Y ;

Kohno, J ;

Nishio, M ;

Takahashi, K ;

Okuda, T ;

Ohnuki, T ;

Komatsubara, S .

JOURNAL OF ANTIBIOTICS, 2000, 53 (02) :105-109

[9] Structures of TMC-95A-D:: Novel proteasome inhibitors from Apiospora montagnei Sacc. TC 1093 [J].

Kohno, J ;

Koguchi, Y ;

Niskio, M ;

Nakao, K ;

Kuroda, M ;

Shimizu, R ;

Ohnuki, T ;

Komatsubara, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (04) :990-995

[10]

MCKILLOP A, 1994, SYNTHESIS-STUTTGART, P31

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