Polyhydroxylated pyrrolizidines. Part 1: Short and highly stereocontrolled syntheses of hyacinthacines

被引:42
作者
Izquierdo, I [1 ]
Plaza, MT [1 ]
Robles, R [1 ]
Franco, F [1 ]
机构
[1] Univ Granada, Dept Organ Chem, Fac Pharm, E-18071 Granada, Spain
关键词
D O I
10.1016/S0957-4166(01)00440-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two short and highly stereocontrolled syntheses for 7a-epi-hyacinthacine A(2) (7-deoxyalexine) 3 and 5,7a-diepihyacinthacine A(3) 4 are, respectively, reported herein. An appropriately protected polyhydroxypyrrolidine. (2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 5, readily available from D-fructose, was chosen as the chiral starting material. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2481 / 2487
页数:7
相关论文
共 15 条
[11]   Synthesis of novel glycosidase-inhibitory hydroxymethyl-substituted polyhydroxylated indolizidines: Ring-expanded analogs of the pyrrolizidine alkaloids alexine and australine [J].
Pearson, WH ;
Hembre, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5546-5556
[12]   GLUCOSIDASE INHIBITORS FOR TREATMENT OF HIV-1 INFECTION [J].
RATNER, L .
AIDS RESEARCH AND HUMAN RETROVIRUSES, 1992, 8 (02) :165-173
[13]   Configurational and conformational analysis of highly oxygenated pyrrolizidines: definitive identification of same naturally occurring 7a-epi-alexines [J].
Wormald, MR ;
Nash, RJ ;
Hrnciar, P ;
White, JD ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2549-2558
[14]  
Yoda H, 2000, SYNLETT, P1001
[15]   Asymmetric total synthesis of natural pyrrolizidine alkaloid, (+)-alexine [J].
Yoda, H ;
Katoh, H ;
Takabe, K .
TETRAHEDRON LETTERS, 2000, 41 (40) :7661-7665