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A formal synthesis of (-)-erinacine B enabled by asymmetric organocatalysis.

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A unified strategy for accessing the core structure of cyathane diterpenoids has been developed, enabling the formal synthesis of (-)-erinacine B. The key feature includes an organocatalyzed asymmetric intramolecular vinylogous… Click to show full abstract

A unified strategy for accessing the core structure of cyathane diterpenoids has been developed, enabling the formal synthesis of (-)-erinacine B. The key feature includes an organocatalyzed asymmetric intramolecular vinylogous aldol reaction for convergently building up the 5-6-6 tricyclic ring system. This strategy also highlights a hydroxyl-directed cyclopropanation/ring opening sequence to stereoselectively set up 1,4-anti and -cis angular-methyl quaternary carbon centers.

Keywords: synthesis erinacine; erinacine enabled; formal synthesis; enabled asymmetric

Journal Title: Chemical communications
Year Published: 2023

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