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

页码：10195 / 10202

页数：8

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