| Autor: |
Somarathne, KK, McCone, Jordan, Brackovic, Amira, Rivera, JLP, Fulton, Jennifer, Russell, E, Field, JJ, Orme, CL, Stirrat, HL, Riesterer, J, Teesdale-Spittle, Paul, Miller, John, Harvey, Joanne |
| Rok vydání: |
2022 |
| Předmět: |
|
| DOI: |
10.25455/wgtn.21637721 |
| Popis: |
The fungal metabolite TAN-2483B has a 2,6-trans-relationship across the pyran ring of its furo[3,4-b]pyran-5-one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side-chain analogues of TAN-2483B. The synthesis relies on ring expansion of a reactive furan ring-fused dibromocyclopropane and alkynylation of the resulting pyran. The furan ring is constructed by palladium-catalysed carbonylative lactonisation. Various side-chains are appended through Wittig-type chemistry. The prepared analogues showed micromolar activity towards cancer cell lines HL-60, 1A9 and MCF-7 and certain human disease-relevant kinases, including Bruton's tyrosine kinase (Btk). |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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