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A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels–Alder Reaction: Stereoselective Synthesis of Octahydro-1H-cyclopenta[cd]isoindole
- Gouse, Shaik, Reddy, Narra Rajashekar, Baskaran, Sundarababu
- Organic letters 2019 v.21 no.10 pp. 3822-3827
- alkaloids, chemical structure, cycloaddition reactions, stereoselective synthesis, stereoselectivity
- 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 BBr₃-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.