Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

The total synthesis of lundurines A–C has been accomplished in racemic and enantiopure forms in 11–13 and 12–14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold­(I)-catalyzed alkyne hydroarylation, a cyclop...

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Veröffentlicht in:Journal of the American Chemical Society 2016-03, Vol.138 (11), p.3671-3674
Hauptverfasser: Kirillova, Mariia S, Muratore, Michael E, Dorel, Ruth, Echavarren, Antonio M
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
catalytic activity
Communication
Condensation
enantiomers
Extrusion
Gold
Isomerization
Migration
nitrogen
olefin
Olefins
Synthesis
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Zusammenfassung:The total synthesis of lundurines A–C has been accomplished in racemic and enantiopure forms in 11–13 and 12–14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold­(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclo­propane retro-ene/ene reaction that streamlines the endgame.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.6b01428