Access to β,γ-diamino acids. Application to the synthesis of 3-deoxyaminostatine

被引：12

作者：

Bouillere, Francelin ^{[1
]}

Guillot, Regis ^{[1
,2
]}

Kouklovsky, Cyrille ^{[1
,2
]}

Alezra, Valerie ^{[1
,2
]}

机构：

[1] Univ Paris Sud, Lab Chim Procedes & Subst Nat, Inst Chim Mol & Mat Orsay, UMR 8182, F-91405 Orsay, France

[2] CNRS, F-91405 Orsay, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 02期

关键词：

STEREOSELECTIVE-SYNTHESIS; 1,2-DIAMINES; HOMOLOGATION; FOLDAMERS; ANALOGS; ENTRY;

D O I：

10.1039/c0ob00370k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of orthogonally protected diastereo-and enantiopure beta,gamma-diamino acids starting from natural alpha-amino acids is described, as well as its application to the synthesis of fully protected 3-deoxyaminostatine.

引用

页码：394 / 399

页数：6

共 32 条

[1] NOVEL RENIN INHIBITORS - SYNTHESIS OF AMINOSTATINE AND COMPARISON WITH STATINE-CONTAINING ANALOGS [J].

ARROWSMITH, RJ ;

CARTER, K ;

DANN, JG ;

DAVIES, DE ;

HARRIS, CJ ;

MORTON, JA ;

LISTER, P ;

ROBINSON, JA ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :755-757

[2] 5-(tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c] pyrimidine-based potent and selective CCK1 receptor antagonists:: Structure-activity relationship studies on the central 1,3-dioxoperhydropyrido[1,2-c]pyrimidine scaffold [J].

Bartolomé-Nebreda, JM ;

García-López, MT ;

González-Muñiz, R ;

Cenarruzabeitia, E ;

Latorre, M ;

Del Río, J ;

Herranz, R .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (24) :4196-4206

[3] ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN [J].

BURGESS, LE ;

MEYERS, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9858-9859

[4] A practical and stereoconservative synthesis of (R)-3-amino-4-(trimethyl-ammonio)butanoate [(R)-aminocarnitine], and its trimethylphosphonium and simple ammonium analogues starting from D-aspartic acid [J].

Calvisi, G ;

Dell'Uomo, N ;

De Angelis, F ;

Dejas, R ;

Giannessi, F ;

Tinti, MO .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4501-4505

[5] Stereocontrolled synthesis of 2,4-diamino-3-hydroxyacids starting from diketopiperazines: A new route for the preparation of statine analogues [J].

Farran, Daniel ;

Toupet, Laic ;

Martinez, Jean ;

Dewynter, Georges .

ORGANIC LETTERS, 2007, 9 (23) :4833-4836

[6] Synthesis of (+)-CP-99,994 via Pd(0)-Catalyzed Asymmetric Allylic and Homoallylic C-H Diamination of Terminal Olefin [J].

Fu, Renzhong ;

Zhao, Baoguo ;

Shi, Yian .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7577-7580

[7] Foldamers: A manifesto [J].

Gellman, SH .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180

[8] Reactivity of chiral α-amidoalkylphenyl sulfones with stabilized carbanions.: Stereoselective synthesis of optically active 1-aminopyrrolizidine [J].

Giri, N ;

Petrini, M ;

Profeta, R .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (21) :7303-7308

[9] Asymmetric aza-henry reaction under phase transfer catalysis:: An experimental and theoretical study [J].

Gomez-Bengoa, Enrique ;

Linden, Anthony ;

Lopez, Rosa ;

Mugica-Mendiola, Idoia ;

Oiarbide, Mike ;

Palomo, Claudio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (25) :7955-7966

[10] A field guide to foldamers [J].

Hill, DJ ;

Mio, MJ ;

Prince, RB ;

Hughes, TS ;

Moore, JS .

CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011

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