| Literature DB >> 30618187 |
Kalpani K Somarathne1, Jordan A J McCone1,2, Amira Brackovic1, José Luis Pinedo Rivera1, J Robin Fulton1, Euan Russell3, Jessica J Field3, Christopher L Orme1, Hedley L Stirrat1, Jasmin Riesterer1, Paul H Teesdale-Spittle2,3, John H Miller3, Joanne E Harvey1,2.
Abstract
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).Entities:
Keywords: TAN-2483B analog; alpha-selective alkynylation; cyclopropane ring expansion; fungal metabolites; furo[3,4-b]pyran-5-one; palladium-catalyzed carbonylation
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Year: 2019 PMID： 30618187 DOI： 10.1002/asia.201801767
Source DB: PubMed Journal: Chem Asian J ISSN： 1861-471X