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Synthesis of Tanshinone IIA and Related Terpenes via a C-H Functionalization Strategy. | LitMetric

Synthesis of Tanshinone IIA and Related Terpenes via a C-H Functionalization Strategy.

Org Lett

Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland A1B 3X7, Canada.

Published: August 2024

AI Article Synopsis

  • The total synthesis of tanshinone IIA, a bioactive diterpene from a Chinese plant, was achieved using a common tetralin building block.
  • Key methods in the synthesis included creating a 3,4-disubstituted furan and employing regioselective C-H functionalization reactions, like Pd-catalyzed iodination and Ir-catalyzed borylation.
  • An intramolecular stanna-Brook type reaction was utilized to build the quinone ring structure of the target compound.

Article Abstract

The total synthesis of tanshinone IIA and related bioactive diterpenes isolated from the Chinese plant 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 -quninone ring of the target molecule.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c02438DOI Listing

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