Formal total synthesis of (-)-balanol:: Concise approach to the hexahydroazepine segment based on RCM

被引：130

作者：

Fürstner, A ^{[1
]}

Thiel, OR ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 06期

关键词：

D O I：

10.1021/jo991611g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of the hexahydroazepine moiety 13 of (-)-balanol 1 is described that comprises only eight steps and is distinctly shorter than all previous reported approaches to this particular compound. Sharpless epoxidation of divinylcarbinol 4 and ring closing alkene metathesis (RCM) reaction for the formation of the heterocyclic scaffold 9 constitute the key transformations of this sequence. The latter reaction is best achieved with catalytic amounts of the ruthenium indenylidene complex 18 recently reported. Furthermore, it is demonstrated that RCM can be successfully carried out even in the presence of an azido function provided that Schrock's molybdenum alkylidene complex Mo(=NAr)(=CHCMe2Ph)[OC(Me)(CF3)(2)](2) (Ar = 2,6-diisopropylphenyl) is used as precatalyst.

引用

页码：1738 / 1742

页数：5

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