Preparation of (+)-Biotin: Process Development and Scale-up

Bifunctional Sulfonamide as Hydrogen Bonding Catalyst in Catalytic Asymmetric Reactions: Concept and Application in the Past Decade

“… [77,78] 2 H ‐pyran‐2,6(3 H )‐dione used as the anhydride substrate could be converted to corresponding enantiopure hemiester in the presence of 39 , and obtained hemiester product could simply be utilized in the short synthesis of ( S )‐pregabalin, which is an antiepileptic drug for treating neuralgia clinically [77] . In 2016, our group realized the synthesis of (+)‐biotin starting from asymmetric desymmetrization of cis ‐1,3‐ bis ‐( p ‐methoxybenzyl)tetrahydro‐2 H ‐furo[3,4‐ d ]imida‐zole‐2,4,6‐trione [78] . Although 110 mol % of 39 was required, the subsequent (+)‐biotin could be obtained in good overall yield and synthesized in kilogram scale.…”

“…Asymmetric alcoholysis of meso-cyclic anhydrides catalyzed by chloramphenicol derived sulfonamide. [78] Although 110 mol % of 39 was required, the subsequent (+)-biotin could be obtained in good overall yield and synthesized in kilogram scale.…”