ol0c02280_si_001.pdf (3.58 MB)
Total Synthesis of Diospyrodin and Its Three Diastereomers
journal contribution
posted on 2020-08-06, 22:20 authored by Takumi Fukuda, Masanori Nagatomo, Masayuki InoueAntibacterial diospyrodin
(1) was synthesized in 13
steps. Et3B and O2 promoted the formation of
an α-alkoxy carbon radical from l-ribose-derived
α-alkoxyacyl telluride 5, which reacted with d-glucose-derived aldehyde 4. The radical addition
realized the convergent assembly of the contiguously hydroxylated
carbon-chain of 3-α and greatly contributed to
streamlining the synthetic route. Compound 3-α was
transformed not only to 1 but also to its three diastereomers
by functional group manipulations.