Biomimetic Enantioselective Total Synthesis of (−)-Mycoleptodiscin A

Biomimetic total synthesis of (−)-mycoleptodiscin A (1) was achieved starting from the enantiopure key intermediate, which was prepared by Friedel–Crafts reaction between 7-methoxyindole and chiral primary allylic alcohol. The crucial step in this synthesis was an intramolecular Friedel–Crafts reaction at C-4 of the indole derivative driven by the EDG/EWG within a compound that was rationally designed to prevent the cyclization reaction at the C-2 positon of indole, thereby successfully providing the complete carbon framework of 1. This intramolecular Friedel–Crafts reaction at C-4 of indole derivative could be applied for the synthesis of other C-4-substituted indole alkaloid natural products.