Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (-)- isocyclocapitelline, and (-)-isochrysotricine

被引：41

作者：

Volz, Frank ^{[1
]}

Wadman, Sipke H. ^{[1
]}

Hoffmann-Roeder, Anja ^{[1
]}

Krause, Norbert ^{[1
]}

机构：

[1] Dortmund Univ Technol, D-44227 Dortmund, Germany

来源：

TETRAHEDRON | 2009年 / 65卷 / 09期

关键词：

Allenes; Chirality transfer; Cycloisomerization; Gold catalysis; Heterocycles; Tetrahydrofurans; MATIERES VEGETALES VOLATILES; 1ST TOTAL-SYNTHESIS; LINALOOL OXIDES; ANNONACEOUS ACETOGENINS; ALPHA-HYDROXYALLENES; SECONDARY ALCOHOLS; ALLYLIC ALCOHOLS; STEREOISOMERS; CIS-LINALYL; CYCLOISOMERIZATION;

D O I：

10.1016/j.tet.2008.11.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1902 / 1910

页数：9

共 93 条

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