Enantioselective Total Synthesis of (-)-BlennolideA

BlennolideA can be synthesized through an enantioselective domino-Wacker/carbonylation/methoxylation reaction of 7a with 96% ee and an enantioselective Wacker oxidation of 7b with 89% ee. Further transformations led to the [alpha],[beta]-unsaturated ester (E)-17, which was subjected to a highly sele...

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Published inChemistry : a European journal Vol. 19; no. 26; pp. 8610 - 8614
Main Authors Tietze, Lutz F, Ma, Ling, Reiner, Johannes R, Jackenkroll, Stefan, Heidemann, Sven
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.06.2013
Subjects
Acylation
Beta
Carbonyls
Chemistry
Esters
Fungi
Metabolites
Oxidation
Synthesis
Transformations
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Summary:BlennolideA can be synthesized through an enantioselective domino-Wacker/carbonylation/methoxylation reaction of 7a with 96% ee and an enantioselective Wacker oxidation of 7b with 89% ee. Further transformations led to the [alpha],[beta]-unsaturated ester (E)-17, which was subjected to a highly selective Michael addition, introducing a methyl group to give 18a. After a threefold oxidation and an intramolecular acylation, the tetrahydroxanthenone 4 was obtained, which could be transformed into (-)-blennolideA (ent-1) in a few steps. [PUBLICATION ABSTRACT]
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201300479