Microbiological Transformations, Part 9. Microbiological Transformations of 1,2,5,6-Tetrahydropyrroloquinolin-4-one and of Derivatives of 1,2,3,5,6,7-Hexahydropyridoquinoline with the Fungus Cunninghamella elegans

Article abstract of DOI:10.1016/S0040-4020(01)82092-5

Incubation of 1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-3(5H)-one with C. elegans resulted in oxidation at the C-7 benzylic position, whereas 1-methyl-1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-5(3H)-one gave products resulting from oxidation at both benzylic positions. cis- and trans-1-Hydroxy-3-methyl-1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-5(3H)-ones were produced on incubation of 5-methyl-1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-3(5H)-one with C. elegans, in addition to trans-1-hydroxy-5-methyl-1,2,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-3(5H)-one.Incubation of 1,2,5,6-tetrahydropyrrolo<3,2,1-i,j>quinolin-4-one with C. elegans resulted in dehydrogenation to 1,2-dihydropyrrolo<3,2,1-i,j>quinolin-4-one.Incubation of 2,3,6,7-tetrahydropyrido<3,2,1-i,j>quinolin-1(5H)-one with C. elegans resulted in benzylic attack at C-7.