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• W3023168434 abstract "An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule as a single regioisomer 30. A second approach employed a tandem cycloreversion/intramolecular [4 + 2] cycloaddition process to afford not only the desired product 30 but also significant quantities of the undesired regioisomer iso-30. An investigation into the reasons for the difference in regioselectivity between these two reactions revealed the intervention of a cycloreversion/cycloaddition pathway at elevated temperatures leading to the formation of iso-30. Experimental evidence supports the hypothesis that iso-30 is the more thermodynamically stable of the two regioisomers." @default.
• W3023168434 created "2020-05-13" @default.
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• W3023168434 date "2005-01-25" @default.
• W3023168434 modified "2023-09-24" @default.
• W3023168434 title "Total Synthesis of Sordaricin" @default.
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• W3023168434 doi "https://doi.org/10.1021/jo048199b" @default.
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