First total synthesis of (+)-hyacinthacine A2

被引:73
作者
Rambaud, L [1 ]
Compain, P [1 ]
Martin, OR [1 ]
机构
[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans, France
关键词
D O I
10.1016/S0957-4166(01)00324-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The first synthesis of (+)-hyacinthacine A(2) has been achieved in six steps from 2,3,5-tri-O-benZyl-D-arabinofuranose in an overall yield of 11%. The structure of this natural product was thus unambiguously established as (1R,2R,3R,7aR)-1,2-dihydroxy-3-1-lydroxymethylpyrrolizidine. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1807 / 1809
页数:3
相关论文
共 28 条
[1]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[2]   New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum:: structural determination and biological activity [J].
Asano, N ;
Kuroi, H ;
Ikeda, K ;
Kizu, H ;
Kameda, Y ;
Kato, A ;
Adachi, I ;
Watson, AA ;
Nash, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :1-8
[3]   VINYLATION ELECTROPHILIC CYCLIZATION OF ALDOPENTOSES - EASY AND STEREOSELECTIVE ACCESS TO C-GLYCOPYRANOSIDES OF RARE SUGARS [J].
BOSCHETTI, A ;
NICOTRA, F ;
PANZA, L ;
RUSSO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4181-4185
[4]   CARBOHYDRATES AS CHIRAL AUXILIARIES - SYNTHESIS OF 2-HYDROXY-BETA-D-GLUCOPYRANOSIDES [J].
CHARETTE, AB ;
MARCOUX, JF ;
COTE, B .
TETRAHEDRON LETTERS, 1991, 32 (49) :7215-7218
[5]  
COMPAIN P, 2001, IN PRESS BIOORG MED
[6]   Synthesis of (+)-casuarine [J].
Denmark, SE ;
Hurd, AR .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :2875-2886
[7]   Enantioselective total syntheses of (+)-castanospermine, (+)-6-epicastanospermine, (+)-australine, and (+)-3-epiaustraline [J].
Denmark, SE ;
Martinborough, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3046-3056
[8]  
FELLOWS L, 1989, Patent No. 897951
[9]   CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].
FU, GC ;
NGUYEN, ST ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857
[10]   Sugar analogues with basic nitrogen in the ring as anti-infectives [J].
Häusler, H ;
Kawakami, RP ;
Mlaker, E ;
Severn, WB ;
Wrodnigg, TM ;
Stütz, AE .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2000, 19 (4-5) :435-449