Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates

被引：41
作者：
Bell, AA
Pickering, L
Watson, AA
Nash, RJ
Pan, YT
Elbein, AD
Fleet, GWJ
机构：
[1] OXFORD CTR MOL SCI,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
[2] INST GRASSLAND & ENVIRONM RES,ABERYSTWYTH SY23 3EB,CARDIGAN,WALES
[3] UNIV ARKANSAS MED SCI,DEPT BIOCHEM & MOL BIOL,LITTLE ROCK,AR 72205
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 33期
基金：
英国工程与自然科学研究理事会; 美国国家卫生研究院; 英国医学研究理事会;
关键词：
D O I：
10.1016/S0040-4039(97)01306-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The key step in the synthesis of four diastereomers of casuarine from eight carbon sugar lactones is the efficient reduction of open chain azidodimesylates by sodium hydrogen telluride [Suzuki-Takaoka reduction] to allow the formation of the pyrrolizidine nucleus by bicyclisation. This is the first report of the synthesis of such highly oxygenated pyrrolizidines. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：5869 / 5872
页数：4
相关论文
共 22 条
[1]  
ASANO N, 1995, J MED CHEM, V38, P2439
[2]   Acetonides of octonolactones [J].
Bell, AA ;
Nash, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 1996, 7 (02) :595-606
[3]   2-hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase) [J].
Bell, AA ;
Pickering, L ;
Watson, AA ;
Nash, RJ ;
Griffiths, RC ;
Jones, MG ;
Fleet, GWJ .
TETRAHEDRON LETTERS, 1996, 37 (47) :8561-8564
[4]   THE EFFECT OF ORAL TREATMENT WITH 6-O-BUTANOYL CASTANOSPERMINE (MDL-28,574) IN THE MURINE ZOSTERIFORM MODEL OF HSV-1 INFECTION [J].
BRIDGES, CG ;
AHMED, SP ;
KANG, MS ;
NASH, RJ ;
PORTER, EA ;
TYMS, AS .
GLYCOBIOLOGY, 1995, 5 (02) :249-253
[5]   ANOMERIC SPECIFICITY OF D-XYLOSE ISOMERASE [J].
COLLYER, CA ;
GOLDBERG, JD ;
VIEHMANN, H ;
BLOW, DM ;
RAMSDEN, NG ;
FLEET, GWJ ;
MONTGOMERY, FJ ;
GRICE, P .
BIOCHEMISTRY, 1992, 31 (48) :12211-12218
[6]   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
[7]   A PROCEDURE FOR ALCOHOL INVERSION USING CESIUM ACETATE [J].
HUFFMAN, JW ;
DESAI, RC .
SYNTHETIC COMMUNICATIONS, 1983, 13 (07) :553-557
[8]   Fagomine isomers and glycosides from Xanthocercis zambesiaca [J].
Kato, A ;
Asano, N ;
Kizu, H ;
Matsui, K ;
Watson, AA ;
Nash, RJ .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (03) :312-314
[9]   SYNTHESIS OF 2-FLUORO-2-DEOXY-MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND SCYLLO-INOSITOL 1,2,4-TRISPHOSPHATE, NOVEL ANALOGS OF THE 2ND MESSENGER MYOINOSITOL 1,4,5-TRISPHOSPHATE [J].
LAMPE, D ;
POTTER, BVL .
TETRAHEDRON LETTERS, 1993, 34 (14) :2365-2368
[10]  
Nash R. J., 1996, ALKALOIDS CHEM BIOL, V11, P346
123