Chapter i: asymmetric total syntheses of (+)-19-deoxyicetexone, (–)-icetexone, and (+)-5-epi-icetexone chapter ii: a practical synthesis of functionalized 6- and 8-hydroxyisochromenes and isocoumarins and a novel route to 8-hydroxyisocoumarins
Grove, Jeremy Lee
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Chapter I: The first asymmetric total syntheses of (+)-19-deoxyicetexone, (–)-icetexone, and (+)-5-epi-icetexone was achieved. This study featured: (1) an enzymatic resolution strategy to construct an asymmetric A-ring; (2) an efficient six step synthesis of the C-ring; (3) the development of a novel Friedel–Crafts cyclialkylation reaction to forge a 6-7-6 cycloheptatriene nucleus. Additionally, our efforts have resulted in a reassignment of the physical data of two epimeric icetexones. Chapter II: A short synthetic route for the preparation of functionalized 8- and 6-hydroxyisochromenes has been developed. Both strategies feature novel intramolecular hydroalkoxylations of conjugated alkynes. Additionally, a novel one-pot oxidation-cyclization-aromatization of a cyclohexadienone-alcohol has resulted in a new method for preparation of functionalized 8-hydroxyisocoumarins.