A Highly Convergent and Biomimetic Total Synthesis of Portentol

An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti−anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, t...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 43; pp. 13800 - 13803
Main Authors Cheng, Bichu, Trauner, Dirk
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2015
Amer Chemical Soc
Subjects
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - metabolism
Biomimetic Materials - chemical synthesis
Biomimetic Materials - chemistry
Biomimetic Materials - metabolism
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Conformation
Oxidation-Reduction
Physical Sciences
Pyrans - chemical synthesis
Pyrans - chemistry
Pyrans - metabolism
Science & Technology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Spiro Compounds - metabolism
POLYPROPIONATE
LACTATE-DERIVED KETONES
ANTI-ALDOL REACTIONS
CHEMISTRY
SUBSTANCES
LICHEN ROCCELLA-PORTENTOSA
UBER FLECHTENINHALTSSTOFFE
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Summary:An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti−anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b10009