Synthesis of substituted cyclohexenyl-based β-amino acids by ring-closing metathesis

被引：31

作者：

Abell, AD ^{[1
]}

Gardiner, J ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 21期

关键词：

D O I：

10.1021/ol0266121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A versatile ring-closing metathesis (RCM) approach has been developed for the preparation of cis and trans cyclohexenyl-based beta-amino acids that are either unsubstituted (3) or substituted (10 and 12) at the alpha-position.

引用

页码：3663 / 3666

页数：4

共 30 条

[1]

Abele S, 1998, HELV CHIM ACTA, V81, P2141, DOI 10.1002/(SICI)1522-2675(19981216)81:12<2141::AID-HLCA2141>3.0.CO

[2]

2-5

[3] (R,R,R)-2,5-diaminocylohexanecarboxylic acid, a building block for water-soluble, helix-forming β-peptides [J].

Appella, DH ;

LePlae, PR ;

Raguse, TL ;

Gellman, SH .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4766-4769

[4] Synthesis and characterization of trans-2-aminocyclohexanecarboxylic acid oligomers:: An unnatural helical secondary structure and implications for β-peptide tertiary structure [J].

Appella, DH ;

Christianson, LA ;

Karle, IL ;

Powell, DR ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6206-6212

[5] Solution conformations of helix-forming β-amino acid homooligomers [J].

Barchi, JJ ;

Huang, XL ;

Appella, DH ;

Christianson, LA ;

Durell, SR ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2711-2718

[6] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[7]

DUAN J, 2001, Patent No. 20010927

[8]

DUPONT PHARM CO, 2001, Patent No. 0170673

[9]

Enders D, 1997, LIEBIGS ANN-RECL, P699

[10] DIASTEREOSELECTIVE ALKYLATION OF 3-AMINOBUTANOIC ACID IN THE 2-POSITION [J].

ESTERMANN, H ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1988, 71 (07) :1824-1839

← 1 2 3 →