An acid-catalyzed
stereoselective epoxide ring-opening/intramolecular
transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct
the phthalide tetrahydroisoquinoline skeleton in one pot. Based on
this strategy, the unified and highly diastereoselective routes for
the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine
were exploited.
Herein, both CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) chiral epoxide ring-opening cascade cyclization to facile and enantioselective synthesis of the core phthalide tetrahydroisoquinoline scaffold of (−)-β-hydrastine are described.
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