%0 Journal Article %J ACS Omega %D 2022 %T Rapid synthesis of the epi-biotin sulfone via tandem S,N-carbonyl migration/aza-michael/spirocyclization and haller-bauer reaction %A Chavan, Subhash P. %A Kalbhor, Dinesh B. %A Gonnade, Rajesh G. %X

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.

%B ACS Omega %V 7 %P 17215-17222 %8 MAY %G eng %N 20 %9 Article %3

Foreign

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4.132

%R 10.1021/acsomega.2c01030