Total Synthesis of (-)-Actinophyllic Acid Enabled by a Key Dual Ir/Amine-Catalyzed Allylation
Xiao Liang1,2, Tian-Yuan Zhang1,2, Chun-Yan Meng1
1State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , China.
Abstract:
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.
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