Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester:: synthesis and biological evaluation of LY411575 analogues

被引：50

作者：

Fuwa, H ^{[1
]}

Okamura, Y ^{[1
]}

Morohashi, Y ^{[1
]}

Tomita, T ^{[1
]}

Iwatsubo, T ^{[1
]}

Kan, T ^{[1
]}

Fukuyama, T ^{[1
]}

Natsugari, H ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 11期

关键词：

medium-sized lactams; Staudinger reaction; aza-Wittig reaction; gamma-secretase inhibitor; structure-activity relationship;

D O I：

10.1016/j.tetlet.2004.01.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient method for the synthesis of medium-sized lactams based on intramolecular Staudinger-aza-Wittig reaction of omega-azido pentafluorophenyl ester has been developed. A variety of 7-10 membered lactams were synthesized in excellent yields. Application of the method to the synthesis of analogues of a potent gamma-secretase inhibitor LY411575 and their biological evaluation are also described. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2323 / 2326

页数：4

共 27 条

[1] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271

[2] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].

Baudoin, O ;

Cesario, M ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207

[3] Intramolecular Staudinger ligation:: A powerful ring-closure method to form medium-sized lactams [J].

David, O ;

Meester, WJN ;

Bieräugel, H ;

Schoemaker, HE ;

Hiemstra, H ;

van Maarseveen, JH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4373-4375

[4] THE AZA-WITTIG REACTION IN HETEROCYCLIC SYNTHESIS - A REVIEW [J].

EGUCHI, S ;

MATSUSHITA, Y ;

YAMASHITA, K .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (02) :209-&

[5] β-secretase as a therapeutic target for inhibitor drugs [J].

Ghosh, AK ;

Hong, L ;

Tang, J .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (11) :1135-1144

[6] RECENT ADVANCES IN THE STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

KASUKHIN, LF .

TETRAHEDRON, 1992, 48 (08) :1353-1406

[7]

HANESSIAN S, 1981, SYNTHESIS-STUTTGART, P396

[8] Solid-phase synthesis of photoaffinity probes: highly efficient incorporation of biotin-tag and cross-linking groups [J].

Kan, T ;

Tominari, Y ;

Morohashi, Y ;

Natsugari, H ;

Tomita, T ;

Iwatsubo, T ;

Fukuyama, T .

CHEMICAL COMMUNICATIONS, 2003, (17) :2244-2245

[9] Stereocontrolled total synthesis of (-)-ephedradine A (orantine) [J].

Kurosawa, W ;

Kan, T ;

Fukuyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8112-8113

[10] Catalytic site-directed γ-secretase complex inhibitors do not discriminate pharmacologically between notch S3 and β-APP cleavages [J].

Lewis, HD ;

Revuelta, BIP ;

Nadin, A ;

Neduvelil, JG ;

Harrison, T ;

Pollack, SJ ;

Shearman, MS .

BIOCHEMISTRY, 2003, 42 (24) :7580-7586

← 1 2 3 →