Synthesis of Segment C of tautomycin was accomplished from 2 D-sugar d
erivatives. New heteroconjugate addition strategy allowed stereocontro
lled syntheses of the 2 sub-segments, C-1 and C-2, and 3 other diaster
eoisomers of the latter. Sub-segments were coupled between sulfone car
banion and epoxide electrophile to furnish the spiro ring moiety of th
e target compound.