Blutzuckersenkende Mittel

摘要

1369800 Carboxy-bicyclo-alkenes and -alkanes and derivatives thereof UPJOHN CO 15 Dec 1971 [14 Jan 1971] 58332/71 Heading C2C [Also in Division A5] The following reaction sequences are described: (A) Bicyclo[2.2.1] heptadiene is oxidized to bicyclo[3.1.0] hex-2-ene-6-endo-carbonaldehyde, which is oxidized to bicyclo[3.1.0] hex- 2-ene-6-endo-carboxylic acid, which is hydrogenated to bicyclo[3.1.0] hexane-6-endo-carboxylic acid which is etherified to methyl bicyclo- [3.1.0] hexane-6-endo-carboxylate which is deesterified to exo-bicyclo[3.1.0] hexane-6-carboxylic acid which is esterified using diazomethane to methyl exo-bicyclo[3.1.0] hexane-6- carboxylate. (B) Exo-bicyclo[3.1.0] hexane-6- formyl chloride is converted by diazomethane and a Wolf rearrangement to methyl exobicyclo[3.1.0] hexane-6-acetate which is deesterified to exo-bicyclo[3.1.0] hexane-6-acetic acid. (C) Exo-bicyclo[3.1.0] hexane-6-formyl chloride is esterified to ethyl exo-bicyclo[3.1.0]- hexane-6-carboxylate.