Terpenoids are the most numerous and structurally diverse natural products. Members of this class have been implemented in medicinal chemistry research and recognized as highly potent therapeutic agents. Their broad spectrum of biological activities renders them medicinally intriguing and their pharmacological properties could be potentially tuned by the mean of synthesizing analogs. Herein we describe two tunable methods for the synthesis of terpenoid frameworks involving a [3,3] sigmatropic (or Cope) rearrangement and an intramolecular allylic alkylation as the key transformations. Both methods utilize inexpensive and readily available carbon sources. Judicious choice of starting materials allows for the synthesis of analogs, which are excellent platforms for further diversification.

Endeavors toward the synthesis of terpenoid frameworks

256th National Meeting (2018)

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