Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

被引：28

作者：

Booker-Milburn, KI

Jenkins, H

Charmant, JPH

Mohr, P

机构：

[1] Univ Bristol, Sch Chem, Struct Chem Lab, Bristol BS8 1TH, Avon, England

[2] Univ Bristol, Sch Chem, CH-4070 Basel, Switzerland

[3] F Hoffman La Roche AG, Pharmaceut Div, Discovery Chem, CH-4070 Basel, Switzerland

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 18期

关键词：

D O I：

10.1021/ol035373u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A short racemic synthesis of kessane from 4-hydroxy-4-methyl-2-cyclohexenone is described using a route that also resulted in the synthesis of the reported structure of pogostol. The key step involves an Fe(III)-mediated tandem radical ring-expansion/cyclization of the cyclopropylsilyl ether 9. No protecting groups are used in the entire sequence. Comparison of the NMR data of synthetic pogostol to that in the literature indicates that the structure originally proposed is incorrect.

引用

页码：3309 / 3312

页数：4

共 22 条

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