Abstract
Synthesis of Segment C of tautomycin was accomplished from two D-sugar derivatives. Pseudoenantiomeric heteroconjugate addition strategy allowed stereocontrolled synthesis of Sub-segment C-1. Sub-segment C-2 and its three diastereoisomers have been synthesized through heteroconjugate addition strategy and Mitsunobu reaction. Sub-segment C-1 (epoxide electrophile) and C2 (sulfone carbanion) were coupled in the presence of boron trifluoride etherate (BF3·OEt2) to furnish Segment C.
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