Total Synthesis and Bioactivity Studies of Fungal Metabolite (-)-TAN-2483B
| Autor: | Kelsi R. Hall, Elysha-Rose Grant, Russell J. Hewitt, Jordan A. J. McCone, David F. Ackerley, Joanne E. Harvey, Kalpani K. Somarathne, Anne Camille La Flamme, Christopher L. Orme |
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| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Cyclopropanes Bicyclic molecule biology Molecular Structure Stereochemistry Organic Chemistry Fungi Total synthesis Alkyne Stereoisomerism Biochemistry Cyclopropane chemistry.chemical_compound Lactones chemistry Side chain biology.protein Bruton's tyrosine kinase Physical and Theoretical Chemistry Carbonylation Pyrans |
| Zdroj: | Organic letters. 22(24) |
| ISSN: | 1523-7052 |
| Popis: | The first total synthesis of (-)-TAN-2483B, a fungal metabolite possessing a densely functionalized furo[3,4-b]pyran-5-one framework, is achieved in 14 steps from d-mannose. Generation of the 2,6-trans-pyran is by cyclopropane ring expansion followed by α-selective alkynylation. Julia-Kocienski olefination introduces the E-propenyl side chain. Alkyne functionalization and carbonylation stereoselectively establish the bicyclic core of (-)-TAN-2483B. Inhibition of kinases Btk and Bmx, bacterial priority pathogens, and cytokine production in splenocytes indicates promising therapeutic potential. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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