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Total synthesis of the proposed structure of briarellin J
Michael T Crimmins1, Mark C Mans, Abimael D Rodríguez
1Kenan, Caudill, Venable, and Murray Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States. crimmins@email.unc.edu
Abstract:
The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.
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