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Synfacts 2024; 20(02): 0111
DOI: 10.1055/s-0043-1772969
DOI: 10.1055/s-0043-1772969
Synthesis of Natural Products
Synthesis of (±)-Aleutianamine
Yu H,
Sercel ZP,
Rezgui SP,
Farhi J,
Virgil SC,
Stoltz BM.
*
California Institute of Technology, Pasadena, USA
Total Synthesis of Aleutianamine.
J. Am. Chem. Soc. 2023;
145: 25533-25537
DOI: 10.1021/jacs.3c10212.
Total Synthesis of Aleutianamine.
J. Am. Chem. Soc. 2023;
145: 25533-25537
DOI: 10.1021/jacs.3c10212.
Key words
(±)-aleutianamine - pyrroloiminoquinone alkaloid - Buchwald–Hartwig amination - Upjohn dihydroxylation
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.
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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.
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Publication History
Article published online:
16 January 2024
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