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Published on: June 13, 2022
Biomimetic Enantioselective Total Synthesis of (-)-Mycoleptodiscin A
Dattatraya H Dethe1, Susanta Kumar Sau1, Samarpita Mahapatra1
1Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur 208016, India rieval.
Abstract:
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.
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