Total synthesis of archaeal 36-membered macrocyclic diether lipid

被引：71

作者：

Eguchi, T ^{[1
]}

Arakawa, K ^{[1
]}

Terachi, T ^{[1
]}

Kakinuma, K ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT CHEM,MEGURO KU,TOKYO 152,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 07期

关键词：

D O I：

10.1021/jo962327h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of archaeal 36-membered macrocyclic diether lipid 2 is reported. The synthesis is based upon stereoselective preparation of functionalized isoprenoid chains, ether-linkage formation between the isaprenoid chains with a glycerol derivative, and the ultimate intramolecular dicarbonyl coupling using low-valent titanium known as McMurry coupling. This synthetic method has successfully provided the first practical route to chemically defined archaeal macrocyclic membrane lipids, which were not available because of the lack of synthetic access. Also described is a highly stereoselective and convenient synthesis of stereochemically homogeneous archaeal biphytanyl glycerol lipid 1.

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页码：1924 / 1933

页数：10

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