Journal
ORGANIC LETTERS
Volume 12, Issue 21, Pages 5028-5031Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102169w
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- The National Institutes of General Medical Sciences [GM60567]
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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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