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Total Synthesis and Bioactivity Studies of Fungal Metabolite (-)-TAN-2483B. | LitMetric
The first total synthesis of (-)-TAN-2483B, a fungal metabolite possessing a densely functionalized furo[3,4-]pyran-5-one framework, is achieved in 14 steps from d-mannose. Generation of the 2,6-pyran is by cyclopropane ring expansion followed by α-selective alkynylation. Julia-Kocienski olefination introduces the -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.
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