Scalable Total Synthesis of Leucascandrolide A Macrolactone Using a Chiral Phosphoric Acid/CuX Combined Catalytic
Shigenobu Umemiya1, Naoya Shinagawa1, Masahiro Terada1
1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Organic Letters
|March 15, 2023
Abstract:
A scalable total synthesis of leucascandrolide A macrolactone has been accomplished with a longest linear sequence of 17 steps from readily available feedstocks in 31.2% yield. The key steps in this synthesis are the enantioselective allylation reaction by chiral phosphoric acid (CPA)/CuBr cooperative catalysis and the diastereoselective catalytic crotylation in the presence of CPA with CuCl. These catalytic reactions can be performed on a gram scale to afford the desired products with excellent stereoselectivities.
