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.