Synthetic studies on tautomycin synthesis of segment C

Article abstract of DOI:10.1016/S0040-4020(97)00229-9

Synthesis of Segment C of tautomycin was accomplished from two D-sugar derivatives. Pseudoenantiomeric heteroconjugate addition strategy allowed stereocontrolled synthesis of Sub-segment C-l. 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.