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

Chem Commun (Camb)

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling 712100, Shaanxi, China.

Published: June 2023

AI Article Synopsis

  • - A new unified strategy has been created to simplify the process of accessing the core structure of diterpenoids, specifically allowing the synthesis of (-)-erinacine B.
  • - The strategy employs an organocatalyzed asymmetric intramolecular vinylogous aldol reaction to efficiently construct a complex 5-6-6 tricyclic ring system.
  • - It also features a method for hydroxyl-directed cyclopropanation and ring opening, which helps in selectively creating 1,4- and angular-methyl quaternary carbon centers.

Article Abstract

A unified strategy for accessing the core structure of 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- and - angular-methyl quaternary carbon centers.

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Source
http://dx.doi.org/10.1039/d3cc01935gDOI Listing

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