Synthesis of 9,10-Phenanthrenes via Palladium-Catalyzed Aryne Annulation by o-Halostyrenes and Formal Synthesis of (±)-Tylophorine

被引：42

作者：

Yao, Tuanli ^{[1
]}

Zhang, Haiming ^{[2
]}

Zhao, Yanna ^{[1
]}

机构：

[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, 6 Xuefu Rd, Xian 710021, Shaanxi, Peoples R China

[2] Genentech Inc, Small Mol Proc Chem, 1 DNA Way, San Francisco, CA 94080 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 11期

关键词：

TYLOPHORA-INDICA; PHENANTHROQUINOLIZIDINE ALKALOIDS; CYNANCHUM-VINCETOXICUM; BIOLOGICAL-ACTIVITY; CYTOTOXIC ACTIVITY; ORGANIC-SYNTHESIS; GENERAL-APPROACH; BUILDING-BLOCKS; LEWIS-ACID; PHENANTHRENES;

D O I：

10.1021/acs.orglett.6b00558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel palladium-catalyzed annulation reaction of in situ generated arynes and o-halostyrenes has been developed. This methodology affords moderate to excellent yields of substituted phenanthrenes and is tolerant of a variety of functional groups such as nitrile, ester, amide, and ketone. This annulation chemistry has been successfully applied to the formal total synthesis of a biologically active alkaloid (+/-)-tylophorine.

引用

页码：2532 / 2535

页数：4

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