Publication:
A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels-Alder Reaction: Stereoselective Synthesis of Octahydro-1 H-cyclopenta[ cd]isoindole

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cris.virtual.department#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtual.department#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtual.departmentIndian Institute of Technology, Madras
cris.virtualsource.department#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtualsource.department#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtualsource.department6a73d7bf-abeb-4caa-8e8e-c9927cb1b528
dc.contributor.authorGouse, Shaik
dc.contributor.authorReddy, Narra Rajashekar
dc.contributor.authorBaskaran, Sundarababu
dc.date.accessioned2023-09-19T14:32:20Z
dc.date.available2023-09-19T14:32:20Z
dc.date.issued17-05-2019
dc.description.abstractFor 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.
dc.identifier.doi10.1021/acs.orglett.9b01267
dc.identifier.issn15237060
dc.identifier.pmid31066566
dc.identifier.scopus2-s2.0-85065852164
dc.identifier.urihttps://apicris.irins.org/handle/IITM2023/27959
dc.relation.ispartofseriesOrganic Letters
dc.sourceOrganic Letters
dc.titleA Domino Aza-Piancatelli Rearrangement/Intramolecular Diels-Alder Reaction: Stereoselective Synthesis of Octahydro-1 H-cyclopenta[ cd]isoindole
dc.typeJournal
dspace.entity.typePublication
oaire.citation.endPage3827
oaire.citation.issue10
oaire.citation.startPage3822
oaire.citation.volume21
oairecerif.author.affiliation#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliation#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliationIndian Institute of Technology, Madras
person.affiliation.cityChennai
person.affiliation.id60025757
person.affiliation.nameIndian Institute of Technology Madras
person.identifier.scopus-author-id57208796482
person.identifier.scopus-author-id57203572743
person.identifier.scopus-author-id7006341682
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