Enantioselective synthesis of the spirotryprostatin A scaffold

被引：63
作者：
Antonchick, Andrey P. [1 ]
Schuster, Hannah [1 ,2 ]
Bruss, Hanna [1 ,2 ]
Schuermann, Markus [2 ]
Preut, Hans [2 ]
Rauh, Daniel [2 ]
Waldmann, Herbert [1 ,2 ]
机构：
[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany
[2] Tech Univ Dortmund, Fak Chem, D-44221 Dortmund, Germany
来源：
TETRAHEDRON | 2011年 / 67卷 / 52期
基金：
欧洲研究理事会;
关键词：
Spirotryprostatin A; All-carbon quaternary spirocenter; 3+2] Cycloaddition; 1,3-Dipolar cycloaddition; Biology-oriented synthesis; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; SOLID-PHASE SYNTHESIS; MAMMALIAN-CELL CYCLE; NATURAL-PRODUCTS; OXINDOLE ALKALOIDS; AZOMETHINE YLIDES; BIOLOGICAL EVALUATION; GARDNERIA ALKALOIDS; CHEMICAL SPACE; CONSTRUCTION;
D O I：
10.1016/j.tet.2011.04.056
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex 3,3'-pyrrolidinyl-spirooxindole core with Fmoc-proline and spontaneous ring closure upon N-deprotection. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10195 / 10202
页数：8
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