Asymmetric,Stereodivergent Synthesis of (−)‐Clusianone Utilizing a Biomimetic Cationic Cyclization |
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| Authors: | Jonathan H. Boyce Prof. Dr. John A. Porco Jr. |
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| Affiliation: | Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD‐BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA) |
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| Abstract: | We report a stereodivergent, asymmetric total synthesis of (?)‐clusianone in six steps from commercial materials. We implement a challenging cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms. Mechanistic studies point to the unique ability of formic acid to mediate the cyclization forming the clusianone framework. |
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| Keywords: | cationic cyclization dearomatization formic acid natural products PPAPs |
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