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Total Synthesis of (−)-Actinophyllic Acid Enabled by a Key Dual Ir/Amine-Catalyzed Allylation
- Liang, Xiao, Zhang, Tian-Yuan, Meng, Chun-Yan, Li, Xue-Dan, Wei, Kun, Yang, Yu-Rong
- Organic letters 2018 v.20 no.15 pp. 4575-4578
- aldehydes, alkylation, allylation, enantioselectivity, moieties
- A synthetic strategy for the catalytic asymmetric total synthesis of (−)-actinophyllic acid is described. This highly efficient and enantioselective approach allows the rapid installation of the four contiguous chiral centers (C16, C15, C20, and C19) by way of a dual Ir/amine catalytic allylation of 2-indolyl vinyl carbinol 6 and an aldol reaction of resultant chiral aldehyde 4a with 2-pyrrolidinone 5. The key indol-3-ylmethanamine moiety and 1-azabicyclo[4.2.1]nonane ring system were readily generated through a selective Mannich-like cyclization and an intramolecular N-alkylation, respectively.