… synthesis of the topically-active carbonic anhydrase inhibitor MK-0507: 5, 6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno [2, 3-b] thiopyran-2-sulfonamide 7, 7- …

…, JW Butcher, T Lamanec, EJJ Grabowski

Index: Blacklock; Sohar; Butcher; Lamanec; Grabowski Journal of Organic Chemistry, 1993 , vol. 58, # 7 p. 1672 - 1679

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Citation Number: 71

Abstract

The key feature in the synthesis of topicdy-active carbonic anhydrase inhibitor MK-0507 (13b) is a Ritter reaction that exhibits an unexpected tendency to proceed with retention of chirality. This phenomenon was further studied on model compounds free from potential diastereomeric effects. A mechanism involving traneannular stabilization of the sp2- hybridized center by sulfone oxygen is proposed with the net result of double inversion. A ...