A Unified Strategy for the Asymmetric Total Syntheses of Diversonol and Lachnone C

被引：45

作者：

Broehmer, Manuel C. ^{[1
]}

Bourcet, Emmanuel ^{[1
]}

Nieger, Martin ^{[2
]}

Braese, Stefan ^{[1
]}

机构：

[1] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

[2] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 49期

关键词：

asymmetric synthesis; diversonol; domino reactions; lachnone; natural products; tetrahydroxanthones; FUNGAL METABOLITES; BLENNOLIDE-C; 4-DEHYDROXYDIVERSONOL; MYCOTOXINS; CHEMISTRY; ALDEHYDES; SCOPE;

D O I：

10.1002/chem.201102192

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified synthetic strategy for the asymmetric syntheses of the natural products diversonol and lachnone C was developed by using the domino vinylogous aldoloxa-Michael reaction as the enantioselective key step. Further transformations include dihydroxylation, lactol-opening by a Wittig-reaction, and lactonization. The obtained chromone lactones, a class of mycotoxins, can further be converted to tetrahydroxanthones by a Dieckmann condensation. This general method allows for the first time the enantioselective access to these classes of natural products and should be applicable to other members of the tetrahydroxanthone and chromone lactone families.

引用

页码：13706 / 13711

页数：6

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