The first total synthesis and structural determination of TMC-66

被引：27

作者：

Hosokawa, Seijiro ^{[1
]}

Fumiyama, Hitoshi ^{[1
]}

Fukuda, Hisato ^{[1
]}

Fukuda, Tomohiro ^{[1
]}

Seki, Masashi ^{[1
]}

Tatsuta, Kuniaki ^{[1
]}

机构：

[1] Waseda Univ, Fac Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 41期

关键词：

total synthesis; structural determination; TMC-66; oxidative coupling; ECE inhibitor;

D O I：

10.1016/j.tetlet.2007.08.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis and structural determination of TMC-66, an ECE inhibitor, was achieved in short steps by efficient construction and coupling of segments. The oxidative coupling with phenols attaching to electron-withdrawing groups was realized with a novel copper(II) reagent. (c) 2007 Elsevier Ltd. All rights reserved.

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收藏

页码：7305 / 7308

页数：4

相关论文

共 26 条

[1] Synthesis of methoxy-2-hydroxy1,4-naphthoquinones and reaction of one isomer with aldehydes under basic conditions [J].

Ameer, F ;

Giles, RGF ;

Green, IR ;

Pearce, R .

SYNTHETIC COMMUNICATIONS, 2004, 34 (07) :1247-1258

[2] TMC-66, a new endothelin converting enzyme inhibitor produced by Streptomyces sp A5008 [J].

Asai, Y ;

Nonaka, N ;

Suzuki, SI ;

Nishio, M ;

Takahashi, K ;

Shima, H ;

Ohmori, K ;

Ohnuki, T ;

Komatsubara, S .

JOURNAL OF ANTIBIOTICS, 1999, 52 (07) :607-612

[3] Highly active and selective catalysts for the formation of α-aryl ketones [J].

Fox, JM ;

Huang, XH ;

Chieffi, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370

[4] 1,2-DIPHENYLETHANE-1,2-DIAMINE - AN EFFECTIVE NMR CHIRAL SOLVATING AGENT FOR CHIRAL CARBOXYLIC-ACIDS [J].

FULWOOD, R ;

PARKER, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (01) :57-64

[5] Palladium-catalyzed intramolecular α-arylation of α-amino acid esters [J].

Gaertzen, O ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :465-475

[6] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[7] OXIDATION OF TETRALONES BY POTASSIUM SUPEROXIDE SOLUBILIZED BY CROWN ETHER [J].

HOCQUAUX, M ;

JACQUET, B ;

VIDRILROBERT, D ;

MAURETTE, MT ;

OLIVEROS, E .

TETRAHEDRON LETTERS, 1984, 25 (05) :533-536

[8] SYNTHESIS OF (+/-)-CERVINOMYCIN-A1 AND (+/-)-CERVINOMYCIN-A2 [J].

KELLY, TR ;

JAGOE, CT ;

LI, Q .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4522-4524

[9] Structure of ericamycin having a 2-azahexaphene ring system [J].

Kondo, S ;

Ikeda, Y ;

Ikeda, D ;

Nishizuka, T ;

Gomi, S .

JOURNAL OF ANTIBIOTICS, 1998, 51 (02) :232-234

[10] 1-ALKENYLATION ON ALPHA-POSITION OF KETONE - PALLADIUM-CATALYZED REACTION OF TIN ENOLATES AND 1-BROMO-1-ALKENES [J].

KOSUGI, M ;

HAGIWARA, I ;

MIGITA, T .

CHEMISTRY LETTERS, 1983, (06) :839-840