Total synthesis of (±)-taiwaniaquinol F (1a) has been accomplished via an efficient Lewis acid-catalyzed Nazarov-type cyclization of aryldiallylcarbinols (±)-2e derived from safranal 7. The methodology works under mild conditions using only 2 mol % of metal triflate as catalyst to afford a previously unknown carbotricyclic core sharing an olefin functionality in excellent yield. The aforementioned methodology also offers enough flexibility to complete the total syntheses of various taiwaniaquinoids, including (±)-taiwaniaquinone H (1d), (±)-dichroanone (1e), (±)-5-epi-taiwaniaquinone G (ent-1h), and (±)-taiwaniaquinol B (1b).
CITATION STYLE
Kakde, B. N., Kumari, P., & Bisai, A. (2015). Total Synthesis of (±)-Taiwaniaquinol F and Related Taiwaniaquinoids. Journal of Organic Chemistry, 80(20), 9889–9899. https://doi.org/10.1021/acs.joc.5b01345
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