The heliannuols are naturally occurring predominantly 7- and 8- membered benzoxacyclic sesquiterpenes, several of which have been shown to serve as serve as allelochemicals. With these classes of compounds in mind, we have developed methodology for the preparation for benzoxocinones, based on intramolecular Nicholas reaction chemistry and γ-carbonyl cations. The scope and limitations of the methodology with respect to arene substitution will be discussed, and the application of this chemistry to the synthesis of heliannuol K methyl ether and heliannuol A will be reported.

Synthesis of benzoxocine heliannuols via the intramolecular Nicholas reaction

2019 Fall National Meeting

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