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Total Synthesis of (+/−)‐Frondosin B and (+/−)‐5‐ epi ‐Liphagal by Using a Concise (4+3) Cycloaddition Approach
Author(s) -
Laplace Duchan R.,
Verbraeken Bart,
Van Hecke Kristof,
Winne Johan M.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303273
Subject(s) - cycloaddition , scope (computer science) , chemistry , combinatorial chemistry , organic chemistry , stereochemistry , computer science , programming language , catalysis
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.