Biology-oriented synthesis of benzopyrano[3, 4-c]pyrrolidines. Issue 12 (15th June 2015)

• Record Type: Journal Article
• Authors: Potowski, Marco; Golz, Christopher; Strohmann, Carsten; Antonchick, Andrey P.; Waldmann, Herbert
• Is Part Of: Bioorganic & medicinal chemistry. Volume 23:Issue 12(2015)
• Page Start: 2895
• Page End: 2903
• Publication Date: 2015-06-15
• Subjects: [2+3] cycloaddition -- Azomethine ylide -- Coumarin -- Biology-oriented synthesis (BIOS) -- Catalysis; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2015.02.044
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: A natural product inspired synthesis of 6, 6, 5-tricyclic compounds via a silver(I)-catalyzed formal 1, 3-dipolar cycloaddition of coumarins with α-iminoesters was developed. The reaction proceeds in a stepwise reaction course under formation of the trans -substituted diastereomer with respect to the 1, 3-dipole and shows a broad substrate scope.