Total Synthesis of (−)-Anominine

The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland−Miescher ketone building blocks, an unusual...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 132; no. 17; pp. 5966 - 5967
Main Authors Bradshaw, Ben, Etxebarria-Jardí, Gorka, Bonjoch, Josep
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.05.2010
Amer Chemical Soc
Subjects
Alkenes - chemical synthesis
Aspergillus - metabolism
Biological Factors - chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Diterpenes - chemical synthesis
Indoles - chemical synthesis
Physical Sciences
Science & Technology
SCLEROTIA
ABSOLUTE-CONFIGURATION
ASPERNOMINE
BIOSYNTHESIS
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Summary:The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland−Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl4-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja101994q