Compound 1 as a key intermediate of 1, 7, 9-trideoxytaxol was synthesized in ten steps from a biosynthetically available taxane, Sinenxan A. The key steps in the synthesis were deoxygenation at C-14, allylic oxidatio...Compound 1 as a key intermediate of 1, 7, 9-trideoxytaxol was synthesized in ten steps from a biosynthetically available taxane, Sinenxan A. The key steps in the synthesis were deoxygenation at C-14, allylic oxidation at C-13 and construction of the oxetane ring.展开更多
Sinenxan A [2α, 5α, 10β, 14β-tetraacetoxytaxa-4(20), 11-diene, 1] was biotransformed by a filamentous fungus, Aspergillus niger JCM 5546, and an unusual taxatetraene [2α, 5α-acetoxytaxa-4(20), 10(11), 12(18), 13...Sinenxan A [2α, 5α, 10β, 14β-tetraacetoxytaxa-4(20), 11-diene, 1] was biotransformed by a filamentous fungus, Aspergillus niger JCM 5546, and an unusual taxatetraene [2α, 5α-acetoxytaxa-4(20), 10(11), 12(18), 13(14)-tetraene, 2], together with two known products, 10β-deacetyl sinenxan A (3) and 10β, 14β-dideacetyl sinenxan A (4) were produced.展开更多
Compound 2 with 14β-hydroxyl group was successfully converted into its epimerized α-counterpart via oxidation - reduction.The elimination product (6) was auto-oxidized to epoxide 8,even in the solid state
基金This research work was financially supported by NNSFC.
文摘Compound 1 as a key intermediate of 1, 7, 9-trideoxytaxol was synthesized in ten steps from a biosynthetically available taxane, Sinenxan A. The key steps in the synthesis were deoxygenation at C-14, allylic oxidation at C-13 and construction of the oxetane ring.
基金supported by the National Natural Science Foundation of China(Project No.30100230)the Japan Society for the Promotion of Science(Project No.1300127).
文摘Sinenxan A [2α, 5α, 10β, 14β-tetraacetoxytaxa-4(20), 11-diene, 1] was biotransformed by a filamentous fungus, Aspergillus niger JCM 5546, and an unusual taxatetraene [2α, 5α-acetoxytaxa-4(20), 10(11), 12(18), 13(14)-tetraene, 2], together with two known products, 10β-deacetyl sinenxan A (3) and 10β, 14β-dideacetyl sinenxan A (4) were produced.
文摘Compound 2 with 14β-hydroxyl group was successfully converted into its epimerized α-counterpart via oxidation - reduction.The elimination product (6) was auto-oxidized to epoxide 8,even in the solid state
