Stereoselective syntheses of the glycosidase inhibitors hyacinthacine A2, hyacinthacine A3 and 5-epi-hyacinthacine A3

被引：25

作者：

Ribes, Celia ^{[2
]}

Falomir, Eva ^{[2
]}

Carda, Miguel ^{[2
]}

Alberto Marco, J. ^{[1
]}

机构：

[1] Univ Valencia, Dept Organ Q, E-46100 Valencia, Spain

[2] Univ Jaume 1, Dept Inorgan & Organ Q, E-12080 Castellon de La Plana, Spain

来源：

TETRAHEDRON | 2009年 / 65卷 / 34期

关键词：

STEREOSPECIFIC TOTAL SYNTHESIS; 1ST TOTAL-SYNTHESIS; PYRROLIZIDINE ALKALOIDS; TETRAHYDROPYRIDINIUM SALTS; NUCLEOPHILIC ADDITIONS; (+)-HYACINTHACINE A(2); CYCLIZATION STRATEGY; BIOLOGICAL-ACTIVITY; A(1); NITRONE;

D O I：

10.1016/j.tet.2009.06.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective syntheses of the naturally occurring glycosidase inhibitors hyacinthacines A(2) and A(3) are reported. In the case of hyacinthacine A(2), the pyrrolizidine system was created from an acyclic precursor via a double cyclization procedure with a one-pot formation of two C-N bonds. In the case of hyacinthacine A(3), the two C-N bonds were created in separate steps. In addition, the non-natural epimer at C-5 of hyacinthacine A(3) was obtained. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6965 / 6971

页数：7

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