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

ABSTRACT: 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.

SUBMITTER: Chavan SP 

PROVIDER: S-EPMC9134234 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature