Synthesis of Hydrocarbazole Derivatives by Oxidative Dearomative Cyclization of Diarylamines Using a Hypervalent Iodine Reagent

被引：11

作者：

Hosoya, Keisuke ^{[1
]}

Iida, Keita ^{[1
]}

Odagi, Minami ^{[1
]}

Nagasawa, Kazuo ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Dept Biotechnol & Life Sci, Koganei, Tokyo 1848588, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 18期

基金：

日本学术振兴会;

关键词：

PHENOL DEAROMATIZATION; ALKALOIDS; CYCLOADDITION; CHEMISTRY; TYROSINE; INDOLES; CORE;

D O I：

10.1021/acs.joc.0c01760

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrocarbazole derivatives bearing a quaternary stereogenic center at C4a were synthesized by means of intramolecular oxidative dearomatization of diarylamines using hypervalent iodine in moderate to good yields. The hydrocarbazole bearing a cyclohexadienone moiety was further converted into the tetracyclic skeletons of Aspidosperma and akuammiline-type alkaloids via regioselective aza-Michael reaction at C4 and at C9a, respectively.

引用

页码：11980 / 11988

页数：9

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