A concise, total synthesis of the TMC-95A/B proteasome inhibitors

被引：59

作者：

Albrecht, BK ^{[1
]}

Williams, RM ^{[1
]}

机构：

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

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2004年 / 101卷 / 33期

关键词：

Julia olefination; Suzuki biaryl coupling; Stille coupling;

D O I：

10.1073/pnas.0308432101

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

A concise, total synthesis of the proteasome inhibitors TMC-95A/B has been accomplished. The synthesis features the use of an L-serine-derived E-selective modified Julia olefination reaction to ultimately control the stereochemical outcome of the highly oxidized tryptophan fragment. Additionally, the limited use of protecting groups at a late stage of the total synthesis allowed for its completion in an efficient manner.

引用

页码：11949 / 11954

页数：6

共 51 条

[11] Lactacystin and clasto-lactacystin beta-lactone modify multiple proteasome beta-subunits and inhibit intracellular protein degradation and major histocompatibility complex class I antigen presentation [J].

Craiu, A ;

Gaczynska, M ;

Akopian, T ;

Gramm, CF ;

Fenteany, G ;

Goldberg, AL ;

Rock, KL .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (20) :13437-13445

[12] 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

[13]

deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153

[14] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[15]

FRIED J, 1973, TETRAHEDRON LETT, V14, P3899

[16] Stereoselective synthesis of enamides by a Peterson reaction manifold [J].

Furstner, A ;

Brehm, C ;

Cancho-Grande, Y .

ORGANIC LETTERS, 2001, 3 (24) :3955-3957

[17] 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

[18] Crystal structure of the 20 S proteasome: TMC-95A complex: A non-covalent proteasome inhibitor [J].

Groll, M ;

Koguchi, Y ;

Huber, R ;

Kohno, J .

JOURNAL OF MOLECULAR BIOLOGY, 2001, 311 (03) :543-548

[19] Total synthesis of TMC-95A [J].

Inoue, M ;

Sakazaki, H ;

Furuyama, H ;

Hirama, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (23) :2654-2657

[20] Stereocontrolled synthesis of the northern part of potent proteasome inhibitor TMC-95A [J].

Inoue, M ;

Furuyama, H ;

Sakazaki, H ;

Hirama, M .

ORGANIC LETTERS, 2001, 3 (18) :2863-2865

← 1 2 3 4 5 6 →