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Dearomative Synthetic Entry into the Altemicidin Alkaloids

Harmange Magnani, Claire S ; Maimone, Thomas J

Journal of the American Chemical Society, 2021-06, Vol.143 (21), p.7935-7939 [Periódico revisado por pares]

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Título:
Dearomative Synthetic Entry into the Altemicidin Alkaloids
Autor: Harmange Magnani, Claire S ; Maimone, Thomas J
Assuntos: Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Molecular Structure ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Sulfur Compounds - chemical synthesis ; Sulfur Compounds - chemistry
É parte de: Journal of the American Chemical Society, 2021-06, Vol.143 (21), p.7935-7939
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: Altemicidin and related Streptomyces-derived monoterpene alkaloids possess dense, highly polar azaindane cores as well as potent cytotoxic and tRNA synthetase inhibitory properties. The congested α-amino acid motif decorating their presumed iridoid-like core structure has proven to be both a synthetic challenge and a biosynthetic mystery to date. Herein, we report a distinct, abiotic strategy to these alkaloids resulting in a concise synthesis of altemicidin from simple chemical feedstocks. Key chemical findings include the exploitation of a dearomative pyridinium addition and dipolar cycloaddition sequence to stereospecifically install the quaternary amine moiety, and a chemoselective molybdenum-mediated double reduction to establish the fully functionalized azaindane nucleus with minimal redox manipulations.
Editor: United States: American Chemical Society
Idioma: Inglês

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