Asymmetric synthesis of (-)-swainsonine

被引：32

作者：

Lindsay, KB ^{[1
]}

Pyne, SG ^{[1
]}

机构：

[1] Univ Wollongong, Dept Chem, Wollongong, NSW 2522, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2004年 / 57卷 / 07期

关键词：

D O I：

10.1071/CH04009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper describes a new synthesis of (-)- swainsonine via the ring-closing metathesis reaction of a substituted 3-allyl-4-vinyloxazolindin-2-one and subsequent diastereoselective syn-dihydroxylation of the resulting pyrrolo[ 1,2-c] oxazol-3-one.

引用

页码：669 / 672

页数：4

共 30 条

[1] A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement [J].

Buschmann, N ;

Rückert, A ;

Blechert, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4325-4329

[2] New synthetic approach to enantiopure bicyclic sulfonium salts:: Swainsonine analogues [J].

Cerè, V ;

Pollicino, S ;

Ricci, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3311-3314

[3] A new strategy for the diastereoselective synthesis of polyfunctionalized pyrrolidines [J].

Davis, AS ;

Gates, NJ ;

Lindsay, KB ;

Tang, MY ;

Pyne, SG .

SYNLETT, 2004, (01) :49-52

[4] L-(+)-swainsonine and other pyrrolidine inhibitors of naringinase: Through an enzymic looking glass from D-mannosidase to L-rhamnosidase? [J].

Davis, B ;

Bell, AA ;

Nash, RJ ;

Watson, AA ;

Griffiths, RC ;

Jones, MG ;

Smith, C ;

Fleet, GWJ .

TETRAHEDRON LETTERS, 1996, 37 (47) :8565-8568

[5]

de Vicente J, 2000, SYNLETT, P53

[6]

Díaz-Pérez P, 2003, SYNLETT, P341

[7] INHIBITION OF LYSOSOMAL ALPHA-MANNOSIDASE BY SWAINSONINE, AN INDOLIZIDINE ALKALOID ISOLATED FROM SWAINSONA-CANESCENS [J].

DORLING, PR ;

HUXTABLE, CR ;

COLEGATE, SM .

BIOCHEMICAL JOURNAL, 1980, 191 (02) :649-651

[8] Synthetic methods for the stereoisomers of swainsonine and its analogues [J].

El Nemr, A .

TETRAHEDRON, 2000, 56 (44) :8579-8629

[9]

Goss PE, 1997, CLIN CANCER RES, V3, P1077

[10]

Goss PE, 1995, CLIN CANCER RES, V1, P935

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