Total Synthesis of (+/−)-Frondosin B and (+/−)-5-epi-Liphagal by Using a Concise (4+3) Cycloaddition Approach

A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl‐type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-01, Vol.20 (1), p.253-262
Main Authors: Laplace, Duchan R., Verbraeken, Bart, Van Hecke, Kristof, Winne, Johan M.
Format: Article
Language:English
Subjects:
Biological Products - chemical synthesis
Biological Products - chemistry
Crystallography, X-Ray
Cycloaddition Reaction
cycloaddition reactions
cycloheptanes
Cycloheptanes - chemistry
furans
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Conformation
natural products
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
total synthesis
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Summary:A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl‐type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven‐membered rings. Cycloheptanes: Furfuryl alcohols serve as effective three‐carbon dienophiles for a wide range of dienes in stereoselective cycloaddition reactions. This efficient reaction has been used to prepare two cycloheptanoid natural products, offering a conceptually straightforward and short synthetic entry into a biologically interesting class of polycyclic meroterpenoids (see scheme; TFA = trifluoroacetic acid).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201303273