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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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
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author Chavan, Subhash P.
Kalbhor, Dinesh B.
Gonnade, Rajesh G.
author_facet Chavan, Subhash P.
Kalbhor, Dinesh B.
Gonnade, Rajesh G.
author_sort Chavan, Subhash P.
collection PubMed
description [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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spelling pubmed-91342342022-05-27 Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction Chavan, Subhash P. Kalbhor, Dinesh B. Gonnade, Rajesh G. ACS Omega [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. American Chemical Society 2022-05-12 /pmc/articles/PMC9134234/ /pubmed/35647474 http://dx.doi.org/10.1021/acsomega.2c01030 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Chavan, Subhash P.
Kalbhor, Dinesh B.
Gonnade, Rajesh G.
Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction
title Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction
title_full Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction
title_fullStr Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction
title_full_unstemmed Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction
title_short Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller–Bauer Reaction
title_sort rapid synthesis of the epi-biotin sulfone via tandem s,n-carbonyl migration/aza-michael/spirocyclization and haller–bauer reaction
url 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
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