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

Chang-Lun Lo, Pavan Sudheer Akula, Bor-Cherng Hong, Gene-Hsiang Lee, Su-Ying Chien

Organic letters 2022 May 13

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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.

Citation

Chang-Lun Lo, Pavan Sudheer Akula, Bor-Cherng Hong, Gene-Hsiang Lee, Su-Ying Chien. Total Synthesis of Ulodione A via a Double-Alkylation and DABCO Promoted Ring-Expansion Rearrangement Sequence. Organic letters. 2022 May 13;24(18):3353-3357