Extending pummerer reaction chemistry. Application to the oxidative cyclization of tryptophan derivatives

被引：46

作者：

Feldman, KS ^{[1
]}

Karatjas, AG ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 17期

关键词：

D O I：

10.1021/ol048974+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective oxidative cyclization of a beta-oxygenated tryptophan derivative is reported. This process, which utilizes a new variant of the Pummerer reaction, may have application in TMC-95A synthesis.

引用

页码：2849 / 2852

页数：4

共 30 条

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

Inoue, M ;

Sakazaki, H ;

Furuyama, H ;

Hirama, M .

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

[12] Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling [J].

Kaiser, M ;

Siciliano, C ;

Assfalg-Machleidt, I ;

Groll, M ;

Milbradt, AG ;

Moroder, L .

ORGANIC LETTERS, 2003, 5 (19) :3435-3437

[13] 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

[14] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[15] AN IMPROVED SYNTHESIS OF DIOXINDOLE-3-PROPIONIC ACID AND SOME TRANSFORMATIONS OF THE C-3 HYDROXYL GROUP [J].

LABROO, RB ;

LABROO, VM ;

KING, MM ;

COHEN, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3637-3642

[16] SUBSTITUTION, OXIDATION AND GROUP PARTICIPATION IN THE BROMINATION OF INDOLES [J].

LAWSON, WB ;

PATCHORNIK, A ;

WITKOP, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (22) :5918-5923

[17] Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR [J].

Lin, SN ;

Yang, ZQ ;

Kwok, BHB ;

Koldobskiy, M ;

Crews, CM ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6347-6355

[18]

Lin SN, 2002, ANGEW CHEM INT EDIT, V41, P512, DOI 10.1002/1521-3773(20020201)41:3<512::AID-ANIE512>3.0.CO

[19]

2-R

[20] 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

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