Synthesis of the AB-Ring Pyranolactone Substructure of Granaticin A

被引：16

作者：

Bartholomaeus, Ruben ^{[1
,2
]}

Bachmann, Janina ^{[1
,2
]}

Mang, Christian ^{[2
]}

Haustedt, Lars Ole ^{[2
]}

Harms, Klaus ^{[1
]}

Koert, Ulrich ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

[2] AnalytiCon Discovery GmbH, D-14473 Potsdam, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 01期

关键词：

Natural products; Lactones; Ozonolysis; Fused-ring systems; Cyclization; PICTET-SPENGLER CYCLIZATION; FRENOLICIN-B; RACEMIC FRENOLICIN; METABOLISM; PRODUCTS;

D O I：

10.1002/ejoc.201201279

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the AB-ring substructure of granaticin A was developed. The pyranolactone moiety was stereoselectively accessed by Sharpless asymmetric dihydroxylation and subsequent oxa-Pictet-Spengler cyclization. The use of BF3 center dot OEt2 resulted in the formation of the cis pyranolactone, whereas the combination of BF3 center dot OEt2 with trifluoroacetic acid led to the trans isomer. The resulting hydroquinones were cleaved selectively by ozonolysis to dicarboxylic acids. An aryl Grignard reagent could be regioselectively added to unsymmetrical anhydrides. As an alternative strategy for the construction of the B-ring, a benzyne-furan cycloaddition could be established.

引用

页码：180 / 190

页数：11

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