Entry into the bi-aryl moiety of the TMC-95 proteasome inhibitors via the Stille protocol

被引：24

作者：

Albrecht, BK ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 15期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(01)00299-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the bi-aryl moiety of the TMC-95 natural products has been achieved via a palladium-catalyzed Stille cross-coupling reaction of an aryl stannane tyrosine derivative and 7-iodoisatin. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2755 / 2757

页数：3

共 12 条

[1] SYNTHESIS OF ORGANOTRIALKYLSTANNANES - THE REACTION BETWEEN ORGANIC HALIDES AND HEXAALKYLDISTANNANES IN THE PRESENCE OF PALLADIUM COMPLEXES [J].

AZIZIAN, H ;

EABORN, C ;

PIDCOCK, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (01) :49-58

[2] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].

FARINA, V ;

KRISHNAN, B ;

MARSHALL, DR ;

ROTH, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5434-5444

[3]

Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01

[4] Crystal structure of epoxomicin:20S proteasome reveals a molecular basis for selectivity of α′,β′-epoxyketone proteasome inhibitors [J].

Groll, M ;

Kim, KB ;

Kairies, N ;

Huber, R ;

Crews, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) :1237-1238

[5]

Hegedus L.S., 1999, TRANSITION METALS SY, V2nd

[6] 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

[7] 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

[8] Enantioselective construction of the oxidized tryptophan fragment of proteasome inhibitors TMC-95A and TMC-95B [J].

Ma, DW ;

Wu, QQ .

TETRAHEDRON LETTERS, 2000, 41 (47) :9089-9093

[9] PROTEASOMES - PROTEIN-DEGRADATION MACHINES OF THE CELL [J].

PETERS, JM .

TRENDS IN BIOCHEMICAL SCIENCES, 1994, 19 (09) :377-382

[10] On iso-nitroacetanilide and its condensation to isatine [J].

Sandmeyer, T .

HELVETICA CHIMICA ACTA, 1919, 2 :234-242

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