Synthesis of Tanshinone IIA and Related Terpenes via a C-H Functionalization Strategy
Nathan Tucker1, Liam H Britt1, Huck K Grover1
1Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland A1B 3X7, Canada.
Abstract:
The total synthesis of tanshinone IIA and related bioactive diterpenes isolated from the Chinese plant Salvia miltiorrhiza was completed from a common tetralin building block. The synthetic route highlights a 3,4-disubstituted furan synthesis and various regioselective C-H functionalization reactions, including a Pd catalyzed iodination and an Ir catalyzed borylation, along with an intramolecular stanna-Brook type reaction to construct the ortho-quninone ring of the target molecule.
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