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A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels-Alder Reaction: Stereoselective Synthesis of Octahydro-1 H-cyclopenta[ cd]isoindole
Shaik Gouse, Narra Rajashekar Reddy,
Published in American Chemical Society
PMID: 31066566
Volume: 21
Issue: 10
Pages: 3822 - 3827
For the first time, an efficient one-pot method for the construction of an angularly fused 5-6-5 aza-tricyclic framework has been developed in a highly stereoselective manner. This domino reaction is a novel combination of aza-Piancatelli rearrangement and intramolecular Diels-Alder reaction, which readily furnishes hexahydro-2a,5-epoxy-cyclopenta[cd]isoindole adducts, bearing six contiguous stereogenic centers in very good yields. The BBr 3 -mediated cleavage of the oxa-bridged adduct results in the formation of octahydro-1H-cyclopenta[cd]isoindole, an aza-tricyclic BCE core of a gracilamine alkaloid. © 2019 American Chemical Society.
About the journal
JournalData powered by TypesetOrganic Letters
PublisherData powered by TypesetAmerican Chemical Society
Open AccessNo