Enantioselective synthesis of m-carboranylalanine, a boron-rich analogue of phenylalanine

被引：20

作者：

Naeslund, C ^{[1
]}

Ghirmai, S ^{[1
]}

Sjöberg, S ^{[1
]}

机构：

[1] Uppsala Univ, Dept Chem, BMC, SE-75124 Uppsala, Sweden

来源：

TETRAHEDRON | 2005年 / 61卷 / 05期

关键词：

m-carboranylalanine; absolute configuration; carborane; Boron neutron capture therapy; asymmetric synthesis; highly lipophilic amino acid;

D O I：

10.1016/j.tet.2004.11.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomers of the highly lipophilic alpha-amino acid m-carboranyl-alanine [3-(1,7-dicarba-closo-dodecaborane(12)-1-yl)-2-aminopropanoic acid], a carborane containing analogue of phenylalanine, have been synthesised via hydroxyamination of the N-acyl derivative formed from 3-(m-carboranyl)propionic acid [3-(1,7-dicarba-closo-dodeca-borane(12)-1-yl)-2-propanoic acid] and Oppolzer's camphor sultam. The enantiomeric excess of both enantiomers of the amino acid was >98%. (S)-Configuration was assigned to the (+)-enantiomer (CH3OH, 589 nm). (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1181 / 1186

页数：6

共 32 条

[1]

ANDERSSON A, 1992, PROGR NEUTRON CAPTUR, V32, P41

[2]

Brattsev V., 1969, Zh Obs. Khim, V39, P1175

[3] DICARBA-CLOSO-DODECABORANES C2B10H12 AND THEIR DERIVATIVES [J].

BREGADZE, VI .

CHEMICAL REVIEWS, 1992, 92 (02) :209-223

[4] Utility of boron clusters for drug design. Relation between estrogen receptor binding affinity and hydrophobicity of phenols bearing various types of carboranyl groups [J].

Endo, Y ;

Yamamoto, K ;

Kagechika, H .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (22) :4089-4092

[5] Potent estrogen agonists based on carborane as a hydrophobic skeletal structure - A new medicinal application of boron clusters [J].

Endo, Y ;

Iijima, T ;

Yamakoshi, Y ;

Fukasawa, H ;

Miyaura, C ;

Inada, M ;

Kubo, A ;

Itai, A .

CHEMISTRY & BIOLOGY, 2001, 8 (04) :341-355

[6] Potent estrogenic agonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore [J].

Endo, Y ;

Iijima, T ;

Yamakoshi, Y ;

Yamaguchi, M ;

Fukasawa, H ;

Shudo, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (09) :1501-1504

[7] Structure-activity study of estrogenic agonists bearing dicarba-closo-dodecaborane.: Effect of geometry and separation distance of hydroxyl groups at the ends of molecules [J].

Endo, Y ;

Iijima, T ;

Yamakoshi, Y ;

Kubo, A ;

Itai, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (23) :3313-3318

[8] Estrogenic antagonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore [J].

Endo, Y ;

Yoshimi, T ;

Iijima, T ;

Yamakoshi, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (24) :3387-3392

[9]

FAUCHERE JL, 1979, HELV CHIM ACTA, V629, P1386

[10] THE ROLE OF CHEMISTRY IN THE DEVELOPMENT OF BORON NEUTRON-CAPTURE THERAPY OF CANCER [J].

HAWTHORNE, MF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :950-984

← 1 2 3 4 →