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. 2020 Mar 20;22(6):2215-2219.
doi: 10.1021/acs.orglett.0c00417. Epub 2020 Feb 27.

Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A

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Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A

Mana Osano et al. Org Lett. .

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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