Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction

[Image: see text] A synthesis of 2-epi-biotin sulfone was accomplished from commercially available l-cysteine. The synthesis features an unprecedented tandem S,N-carbonyl migration/aza-Michael/spirocyclization reaction from an l-cysteine-derived enone with aq. ammonia, in which three new sigma bonds...

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Detalles Bibliográficos
Autores principales: Chavan, Subhash P., Kalbhor, Dinesh B., Gonnade, Rajesh G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9134234/
https://www.ncbi.nlm.nih.gov/pubmed/35647474
http://dx.doi.org/10.1021/acsomega.2c01030
Descripción
Sumario:[Image: see text] A synthesis of 2-epi-biotin sulfone was accomplished from commercially available l-cysteine. The synthesis features an unprecedented tandem S,N-carbonyl migration/aza-Michael/spirocyclization reaction from an l-cysteine-derived enone with aq. ammonia, in which three new sigma bonds and two rings are formed. In addition, the synthesis includes a highly diastereoselective late-stage Haller–Bauer reaction of sulfone for direct introduction of the carbon side chain.

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