Total synthesis of Japanese hop ether using an efficient intramolecular Pauson-Khand reaction

被引：17

作者：

Caldwell, JJ ^{[1
]}

Cameron, ID ^{[1
]}

Christie, SDR ^{[1
]}

Hay, AM ^{[1
]}

Johnstone, C ^{[1
]}

Kerr, WJ ^{[1
]}

Murray, A ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, W CHEM, Glasgow G1 1XL, Lanark, Scotland

来源：

SYNTHESIS-STUTTGART | 2005年 / 19期

关键词：

amine N-oxides; cyclopentenones; natural products; Pauson-Khand cyclizations; stereoselectivity;

D O I：

10.1055/s-2005-918459

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The naturally occurring monoterpene Japanese Hop Ether has been synthesised in 14 steps in an overall yield of 29%. The key step of the synthesis. an intramolecular Pauson-Khand reaction, has been shown to proceed in good to excellent yield under mild A-oxide promotion conditions and with complete retention of alkene Stereochemistry (for both cis- and trans-alkenes) in the product cyclopentenone.

引用

页码：3293 / 3296

页数：4

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