One-Pot Synthesis of Cycloocta[b]indole Through Formal [5+3] Cycloaddition Using Donor-Acceptor Cyclopropanes

被引：19

作者：

Okabe, Akito ^{[1
]}

Harada, Shinji ^{[1
,2
]}

Takeda, Takuya ^{[1
]}

Nishida, Atsushi ^{[1
,2
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan

[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 24期

基金：

日本学术振兴会;

关键词：

Medium-ring compounds; Synthetic methods; Cyclization; Catalysis; Indole; ENANTIOSPECIFIC TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; METAL-CATALYZED CYCLOADDITIONS; INDOLE ALKALOIDS TALPININE; C-H ACTIVATION; 8-MEMBERED RINGS; DERIVATIVES; SARPAGINE; CYCLIZATION; CONSTRUCTION;

D O I：

10.1002/ejoc.201900610

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to cycloocta[b]indole through formal [5+3] cycloaddition was developed. This methodology was realized by using an indole derivative as a C5 unit and a cyclopropane derivative as a C3 unit. These two units have both donor and acceptor properties. Two carbon-carbon bonds were formed stepwise by the successive addition of a Lewis acidic catalyst and a Bronsted base. The reaction could be performed as a one-pot process. Optically active cycloocta[b]indole was also synthesized by using this methodology with a chiral cyclopropane as a C3 substrate.

引用

页码：3916 / 3920

页数：5

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