Synthesis
DOI: 10.1055/a-2501-4796
feature

A Revised Protecting Group Strategy enables a Divergent Synthesis of Prenylated Isoflavones from Psoralea corylifolia

Sarah von Chamier Gliszczinski
1   Institut für Chemie, Universität Potsdam, Potsdam, Germany
,
Eric Sperlich
1   Institut für Chemie, Universität Potsdam, Potsdam, Germany
,
Alexandra Kelling
1   Institut für Chemie, Universität Potsdam, Potsdam, Germany
,
George Kwesiga
2   Chemistry, Kabale University, Kabale, Uganda (Ringgold ID: RIN323124)
1   Institut für Chemie, Universität Potsdam, Potsdam, Germany
,
1   Institut für Chemie, Universität Potsdam, Potsdam, Germany
› Author Affiliations
Supported by: Deutscher Akademischer Austauschdienst 57381412

Three bioactive prenylated isoflavone natural products were synthesized for the first time, using a combination of Pd-catalyzed Suzuki-Miyaura-coupling for installing the B-ring, microwave promoted Claisen-rearrangement of allyl ethers, and Ru-catalyzed olefin cross metathesis for obtaining the prenyl substituents. Careful consideration of the protecting group strategy turned out to be vital for the success of these total syntheses.



Publication History

Received: 12 November 2024

Accepted after revision: 12 December 2024

Accepted Manuscript online:
12 December 2024

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