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...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2015-11, Vol.137 (43), p.13800-13803
Main Authors: Cheng, Bichu, Trauner, Dirk
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - metabolism
Biomimetic Materials - chemical synthesis
Biomimetic Materials - chemistry
Biomimetic Materials - metabolism
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Conformation
Oxidation-Reduction
Pyrans - chemical synthesis
Pyrans - chemistry
Pyrans - metabolism
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Spiro Compounds - metabolism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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