Synthesis of enantiomerically pure cyclopentene building blocks

被引：27

作者：

Tietze, Lutz F. ^{[1
]}

Stadler, Christian ^{[1
]}

Boehnke, Niels ^{[1
]}

Brasche, Gordon ^{[1
]}

Grube, Alexander ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

SYNLETT | 2007年 / 03期

关键词：

cyclopentenes; enzymes; benzyloxymethyl cuprate; spinosyns; Claisen-Ireland rearrangement;

D O I：

10.1055/s-2007-967937

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of the enantiomerically pure cis-annulated cyclopentenes 2 and ent-2 was established by the use of an enzymatic transesterification and hydrolysis, respectively, followed by an S(N)2-type Substitution with a benzyloxymethyl cuprate and a sigmatropic rearrangement. The advantage of this approach is the short sequence combined with an excellent overall yield and an enantiomeric excess of 99%.

引用

页码：485 / 487

页数：3

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