4.8 Article

Total Synthesis of Ulodione A via a Double-Alkylation and DABCO Promoted Ring-Expansion Rearrangement Sequence

Journal

ORGANIC LETTERS
Volume 24, Issue 18, Pages 3353-3357

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01038

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Funding

  1. Ministry of Science and Technology (MOST, Taiwan)

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The first total synthesis of ulodione A has been achieved through a series of reactions, including the key-step reactions of DIPEA-promoted dialkytion of 1,3-cyclopentadione with a bromonitroolefin and DABCO promoted/catalytic semipinacol-like ring-expansion rearrangement, with regioselective transformation of the nitrocyclohexane intermediates to their cyclopentenone counterparts. The structures of six products were confirmed by X-ray crystallography.
First total synthesis of ulodione A has been achieved via the key-step reactions of DIPEA-promoted dialkytion of 1,3-cyclopentadione with a bromonitroolefin and DABCO promoted/catalytic semipinacol-like ring-expansion rearrangement, with regioselective transformation of the nitrocyclohexane intermediates to their cyclopentenone counterparts via a sequence of reactions in a one-pot operation. Structures of six products were unequivocally established by X-ray crystallography.

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