A formal synthesis of (-)-swainsonine from a chiral aziridine

被引：28

作者：

Choi, Hwan Geun ^{[1
]}

Kwon, Ji Hye ^{[1
]}

Kim, Jong Chan ^{[1
]}

Lee, Won Koo ^{[1
]}

Eum, Heesung ^{[2
]}

Ha, Hyun-Joon ^{[2
]}

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

[2] Hankuk Univ Foreign Studies, Dept Chem, Yongin 449719, Kyunggi Do, South Korea

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 25期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DECARBONYLATION; SWAINSONINE; INHIBITORS; ALCOHOLS; ANALOGS;

D O I：

10.1016/j.tetlet.2010.04.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal synthesis of enantiomerically pure (-)-swainsonine was successfully achieved using intramolecular cyclization of the amino alcohol 4 which was derived from a readily available 1-(R)-alpha-methylbenzylaziridine-2-carboxylic acid (-)-menthol ester 6. (C) 2010 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3284 / 3285

页数：2

相关论文

共 25 条

[11] Efficient synthesis of Ephedra alkaloid analogues using an enantiomerically pure N-[(R)-(+)-alpha-methylbenzyl]aziridine-2-carboxaldehyde [J].

Hwang, GI ;

Chung, JH ;

Lee, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6183-6188

[12] STEREOSELECTIVE SYNTHESIS OF THE HYDROXY AMINO-ACID MOIETY OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77 [J].

KAWAI, A ;

HARA, O ;

HAMADA, Y ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1988, 29 (48) :6331-6334

[13] Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases [J].

Kim, JW ;

Kim, YW ;

Inagaki, Y ;

Hwang, YA ;

Mitsutake, S ;

Ryu, YW ;

Lee, WK ;

Ha, HJ ;

Park, CS ;

Igarashi, Y .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (10) :3475-3485

[14] An efficient synthesis of chiral terminal 1,2-diamines using an enantiomerically pure [1-(1′R)methylbenzyl]aziridine-2-yl]methanol [J].

Lee, Baeck Kyoung ;

Kim, Min Sung ;

Hahm, Heung Sik ;

Kim, Dong Sub ;

Lee, Won Koo ;

Ha, Hyun-Joon .

TETRAHEDRON, 2006, 62 (35) :8393-8397

[15] Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine [J].

Lindsay, KB ;

Pyne, SG .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7774-7780

[16] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

[17] General approach to glycosidase inhibitors.: Enantioselective synthesis of deoxymannojirimycin and swainsonine [J].

Martín, R ;

Murruzzu, C ;

Pericàs, MA ;

Riera, A .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2325-2328

[18] Decarbonylation of α-tertiary amino acids application to the synthesis of polyhydroxylated indolizidines from D,L-pipecolic acid [J].

Martín-López, MJ ;

Rodriguez, R ;

Bermejo, F .

TETRAHEDRON, 1998, 54 (38) :11623-11636

[19]

PEARLMAN WM, 1967, TETRAHEDRON LETT, P1663

[20] Recent developments on the synthesis of (-)-swainsonine and analogues [J].

Pyne, SG .

CURRENT ORGANIC SYNTHESIS, 2005, 2 (01) :39-57