Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C

被引：40

作者：

Martin-Torres, Inmaculada ^{[1
,2
]}

Ogalla, Gala ^{[1
,2
]}

Yang, Jin-Ming ^{[1
]}

Rinaldi, Antonia ^{[1
]}

Echavarren, Antonio M. ^{[1
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, C Marcel Li Domingo S-N, Tarragona 43007, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 17期

基金：

欧盟地平线“2020”; 欧洲研究理事会;

关键词：

alkoxycyclization; asymmetric synthesis; gold(I) cavitands; natural product synthesis;

D O I：

10.1002/anie.202017035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities.

引用

页码：9339 / 9344

页数：6

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