The cationic cascade route to longifolene |
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Authors: | Ho Gregory A Nouri Dustin H Tantillo Dean J |
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Institution: | Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, CA 95616, USA. |
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Abstract: | W. S. Johnson's total synthesis of the sesquiterpenoid longifolene is a classic example of the power of cationic polycyclizations for constructing complex molecular architectures. Herein we revisit the key polycyclization step of this synthesis using hybrid Hartree-Fock/density functional theory calculations and validate the feasibility of Johnson's proposed mechanism. We also explore perturbations to the 3-center 2-electron bonding array in a key intermediate that result from changing the polycyclic framework in which it is embedded. |
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