Synthesis of Segment C of Tautomycin

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Abstract
Synthesis of Segment C of tautomycin was accomplished from 2 D-sugar derivatives. New heteroconjugate addition strategy allowed stereocontrolled syntheses of the 2 sub-segments, C-1 and C-2, and 3 other diastereoisomers of the latter. Sub-segments were coupled between sulfone carbanion and epoxide electrophile to furnish the spiro ring moiety of the target compound.

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