Total synthesis of (+/-)-frondosin B and (+/-)-5-epi-liphagal by using a concise (4+3) cycloaddition approach
Duchan R Laplace1, Bart Verbraeken, Kristof Van Hecke
1Department of Organic Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Gent (Belgium).
Abstract:
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.
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