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  • Title: Enantiocontrolled synthesis of a tetracyclic aminal corresponding to the core subunit of diazonamide A.
    Author: Peris G, Vedejs E.
    Journal: J Org Chem; 2015 Mar 20; 80(6):3050-7. PubMed ID: 25705992.
    Abstract:
    A chiral benzylic ether serves as an auxiliary for oxindole carboxylation (dr 5.2:1.0) that sets C10 configuration in a potential diazonamide precursor. The chiral substituent allows diastereomer separation and departs during a subsequent acid-catalyzed ring closure to form a tetracyclic aminal. With suitable N-protection, crystallization affords the aminal with 98-99% ee.
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