An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)-talcarpine and (-)-anhydromacrosalhine-methine

被引：37

作者：

Liao, Xuebin ^{[1
]}

Zhou, Hao ^{[1
]}

Yu, Jianming ^{[1
]}

Cook, James M. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 23期

关键词：

D O I：

10.1021/jo061652u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intramolecular Pd-catalyzed alpha-vinylation process is described. This cyclization has been employed for the enantiospecific total synthesis of gram quantities of both (+)-macroline 3 and the macroline equivalent 4. This sequence is compared to the enolate-driven cross-coupling process. The intermediate 4 was also converted into (-)-alstonerine 1 via modification of an intramolecular Tsuji-Wacker oxidation. This sequence resulted in an improved total synthesis of (-)-talcarpine 5 and (-)-anhydromacrosalhine-methine 6 as well.

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页码：8884 / 8890

页数：7

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