A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene |
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Authors: | David J.-Y.D. Bon Anthony C. Willis |
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Affiliation: | Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia |
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Abstract: | The first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered ring within this framework and various functional group interconversions then provide the title compound 2. |
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Keywords: | Chemoenzymatic Connatusin B Diels-Alder Oxa-di-π-methane Photochemistry Sesquiterpene |
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