Open AccessConcise 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.