Total synthesis of racemic,natural (+) and unnatural (−) scorzocreticin |
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Authors: | BTV Srinivas Amarnath R MaadhurSreedhar Bojja |
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Institution: | Inorganic & Physical Chemistry Division, Indian Institute of Chemical Technology (Council of Scientific & Industrial Research), Hyderabad 500607, India |
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Abstract: | The first total synthesis of racemic scorzocreticin and its pure enantiomers is described from readily available 3,5-dihydroxybenzoic acid. The key steps include Wittig olefination, asymmetric Me-CBS (Corey–Bakshi–Shibata) oxazaborolidine reduction, and improved Pd-catalyzed intramolecular lactonization reactions. Both the (S)-natural and (R)-unnatural enantiomers of scorzocreticin have been synthesized in excellent enantioselectivities (>99% and 99% ee, respectively). In addition, 1,10-phenanthroline, a bidentate N-ligand was employed in palladium-catalyzed intramolecular carbonylation/lactonization reaction for the construction of 3,4-dihydroisocoumarin ring. |
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Keywords: | Intramolecular carbonylation Lactonization Scorzocreticin Total synthesis |
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