The stereocontrolled synthesis of the southern lactone 17 of
boromycin and of the northern segments of both boromycin and aplasmomycin
are described. The syntheses begin with enantioselective
epoxidation of 3-buten-2-ol (42) to provide the optically active
2(S),3(R) epoxy alcohol 43. The absolute configuration was confirmed
by preparing 43 from (-)-2,3-dihydroxybutyric...
Several approaches to the synthesis of methymycin were
investigated. Segment A (39), containing functionality corresponding
to C-9, 10, and 11 of methynolide was made in
six steps from propionaldehyde in an overall yield of 37%.
Oxidation of 34 with silver nitrate gave 35 which, upon hydroxylation
with hydrogen peroxide, gave...
Alkylation of propylene oxide with 2-lithiofuran gave alcohol I,
which was smoothly converted to acetylfuran II. hydrogenation of II
over rhodium on charcoal followed by Jones' oxidation afforded ketone
III. Further transformation into IV was accomplished via a Wittig
reaction followed by saponification with methanolic sodium hydroxide.
Hydroboration of the...