Contributors: Erick M. Carreira, Bilal Kicin
Significance
Stoltz and co-workers report the total synthesis of the recently isolated pyrroloiminoquinone alkaloid (±)-aleutianamine. Key to their approach is a palladium-catalyzed dearomative thiophene functionalization to construct the [3.3.1]ring system and the thioimidate.
Comment
Tricycle E was accessed from hydrazine A in five steps. Reductive amination of amidothio-phene G and subsequent bromination yielded tertiary amine H. Treatment with Pd(dba)2 and XPhos in the presence of a base led to dearomative cyclization and acetamide cleavage, resulting in thioimidate J.
Yu H, Sercel ZP, Rezgui SP, Farhi J, Virgil SC, Stoltz BM. * California Institute of Technology, Pasadena, USA
J. Am. Chem. Soc. 2023; 145: 25533-25537
DOI: 10.1021/jacs.3c10212.
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