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

[1] A concise formal total synthesis of TMC-95A/B proteasome inhibitors [J].

Albrecht, BK ;

Williams, RM .

ORGANIC LETTERS, 2003, 5 (02) :197-200

[2] Synthesis of macrocyclic peptide analogues of proteasome inhibitor TMC-95A [J].

Berthelot, A ;

Piguel, S ;

Le Dour, G ;

Vidal, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9835-9838

[3] TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN [J].

BOGER, DL ;

PATANE, MA ;

ZHOU, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8544-8556

[4] Chemoselective Michael reactions on pyroglutamates.: Expeditious synthesis of spiro-bis-γ-lactams as β-turn peptidomimetics [J].

Braña, MF ;

Garranzo, M ;

de Pascual-Teresa, B ;

Pérez-Castells, J ;

Torres, MR .

TETRAHEDRON, 2002, 58 (24) :4825-4836

[5] TOTAL SYNTHESIS OF TRYPTOQUIVALINE-G [J].

BUCHI, G ;

DESHONG, PR ;

KATSUMURA, S ;

SUGIMURA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :5084-5086

[6] REACTION OF TRYPTOPHAN DERIVATIVES WITH PHENYLSULFENYL CHLORIDE AND PHENYLSELENENYL BROMIDE [J].

CRICH, D ;

DAVIES, JW .

TETRAHEDRON LETTERS, 1989, 30 (32) :4307-4308

[7] Use of Stang's reagent, PhI(CN)OTf, to promote Pummerer-like oxidative cyclization of 2-(phenylthio)indoles [J].

Feldman, KS ;

Vidulova, DB .

TETRAHEDRON LETTERS, 2004, 45 (26) :5035-5037

[8] Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives [J].

Feldman, KS ;

Vidulova, DB .

ORGANIC LETTERS, 2004, 6 (11) :1869-1871

[9] REACTIONS OF N-BROMOSUCCINIMIDE + INDOLES . SIMPLE SYNTHESIS OF 3-BROMOOXINDOLES [J].

HINMAN, RL ;

BAUMAN, CP .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) :1206-+

[10] REACTIONS OF 3-BROMOOXINDOLES - SYNTHESIS OF 3-METHYLENEOXINDOLE [J].

HINMAN, RL ;

BAUMAN, CP .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (08) :2431-&

← 1 2 3 →