The total synthesis of a cyclopropenone-containing sesquiterpenoid has been achieved in eight steps and 9.8% overall yield starting from commercially available valencene. Plants of the Inula genus have long been used in traditional Chinese medicine for treatment of bronchitis and influenza, prompting interest in determining which compounds are responsible for the purported benefits. The scarcity and potential anti-inflammatory activity of this natural product make it an attractive target for total synthesis. Key steps in our route include kinetic protonation of an enolate to establish a key stereocenter and a stereoconvergent epoxide opening taking advantage of the trans-diaxial effect. Samples of the natural product and intermediates along the synthetic route have been characterized using modern spectroscopic techniques and will be submitted to Eli Lilly’s Open Innovation Drug Discovery (OIDD) program to screen for evidence of novel medical and biological applications.

Total synthesis of a cyclopropenone-containing sesquiterpenoid

2019 Spring National Meeting

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