Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A
- PMID: 32105087
- DOI: 10.1021/acs.orglett.0c00417
Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A
Abstract
A new variant of the intramolecular Diels-Alder oxazole (IMDAO) cycloaddition that provides direct access to 6-azaindoles was developed. The IMDAO reaction was applied in a total synthesis of the aminophenylpyrrole-derived alkaloid marinoquinoline A, also featuring the use of a Curtius reaction for preparation of a 5-aminooxazole, a propargylic C,H-bond insertion, an in situ alkyne-allene isomerization, and a ruthenium-catalyzed cycloisomerization for benzene ring annulation to the 6-azaindole.
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