Preparation of Amino-Substituted Indenes and 1,4-Dihydronaphthalenes Using a One-Pot Multireaction Approach: Total Synthesis of Oxybenzo[c]phenanthridine Alkaloids

被引：27

作者：

Calder, Ewen D. D. ^{[1
]}

McGonagle, Fiona I. ^{[1
]}

Harkiss, Alexander H. ^{[1
]}

McGonagle, Grant A. ^{[1
]}

Sutherland, Andrew ^{[1
]}

机构：

[1] Univ Glasgow, Sch Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 16期

基金：

英国工程与自然科学研究理事会;

关键词：

PHOSPHINE COMBINATION SYSTEM; NICKEL-CATALYZED ANNULATION; CROSS-COUPLING REACTIONS; ISOQUINOLINE ALKALOIDS; BETA-PHENYLETHYLAMINES; METATHESIS CATALYSTS; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; FACILE SYNTHESIS; HONG-KONG;

D O I：

10.1021/jo5014492

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine.An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.

引用

页码：7633 / 7648

页数：16

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