Synthesis of the BCD-Ring Substructure of Granaticin A

被引：4

作者：

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 | 2012年 / 2012卷 / 33期

关键词：

Asymmetric synthesis; Natural products; Oxygen heterocycles; Quinones; STREPTOMYCES VIOLACEORUBER TU22; BIOSYNTHETIC GENE-CLUSTER; REGIOSELECTIVE SYNTHESIS; ANTHRAQUINONES; METABOLISM; PRODUCTS;

D O I：

10.1002/ejoc.201201104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The BCD-ring substructure of granaticin A was synthesised following a new approach for the construction of the naphthoquinone moiety. The 2-oxabicyclo[2.2.2]oct-5-ene substructure was accessible stereoselectively using a Sharpless asymmetric dihydroxylation and a diastereoselective ketone reduction in combination with Yoshii's route. The naphthoquinone B-ring was prepared by addition of an aryllithium intermediate to an anhydride followed by a FriedelCrafts cyclisation mediated by AlCl3 and Mg(OTf)2. The success of the FriedelCrafts cyclisation relied on the conversion of the ketone-carboxylic acid into a lactone acetal.

引用

页码：6562 / 6569

页数：8

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