Vic-Tricarbonyl Compounds: Synthesis of (±)-9-epi-Wailupemycin A

Tobias Seitz; Klaus Harms; Ulrich Koert

doi:10.1055/s-0033-1340313

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(03): 381-386
DOI: 10.1055/s-0033-1340313

paper

Vic-Tricarbonyl Compounds: Synthesis of (±)-9-epi-Wailupemycin A

Tobias Seitz

Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany Fax: +49(6421)2825677 eMail: koert@chemie.uni-marburg.de

,

Klaus Harms

Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany Fax: +49(6421)2825677 eMail: koert@chemie.uni-marburg.de

,

Ulrich Koert*

Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany Fax: +49(6421)2825677 eMail: koert@chemie.uni-marburg.de

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Abstract

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Dedicated to Prof. R. W. Hoffmann on the occasion of his 80^th birthday

Abstract

A synthesis of the 9-epimer of the marine natural product wailupemycin A is reported. The key reaction sequence consists of a diastereoselective enamine addition to a tricarbonyl monohydrate, the formation of an enol silyl acetal, and finally the stereocontrolled addition of the α-pyrone substructure.

Key words

vicinal tricarbonyl compound - enamine - α-pyrone - natural products - stereoselective synthesis

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Referenzen

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