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Concise Formal Synthesis of the Pseudopterosins via Anionic Oxy-Cope/Transannular Michael Addition Cascade.

ABSTRACT: An anionic oxy-Cope/transannular Michael addition cascade converts a spirocyclic architecture-readily available by Diels-Alder cycloaddition-into the hydrophenalene carbon skeleton of the pseudopterosin aglycones. Oxidation of the resulting cyclohexenone ring to the phenol that is characteristic of the targets completes a short formal synthesis.

SUBMITTER: Ramella V

PROVIDER: S-EPMC7278522 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Concise Formal Synthesis of the Pseudopterosins via Anionic Oxy-Cope/Transannular Michael Addition Cascade.

Ramella Vincenzo V Roosen Philipp C PC Vanderwal Christopher D CD

Organic letters 20200220 8

An anionic oxy-Cope/transannular Michael addition cascade converts a spirocyclic architecture-readily available by Diels-Alder cycloaddition-into the hydrophenalene carbon skeleton of the pseudopterosin aglycones. Oxidation of the resulting cyclohexenone ring to the phenol that is characteristic of the targets completes a short formal synthesis. ...[more]

PMID: 32077289

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