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

Vincenzo Ramella | Zendy; Philipp C. Roosen | Zendy; Christopher D. Vanderwal | Zendy

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

Author(s) -

Vincenzo Ramella,

Philipp C. Roosen,

Christopher D. Vanderwal

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00486

Subject(s) - michael reaction , chemistry , cyclohexenone , cascade , cycloaddition , phenol , carbon skeleton , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , chromatography

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.

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