Abstract
Abstract The synthesis of Segment B/C corresponding to the C26 through to the C1 positions of tautomycin was achieved by coupling between Segment B (an epoxide) and Segment C (a sulfone carbanion) in the presence of boron trifluoride etherate (BF 3 ·OEt 2 ). Two routes have been developed in esterification of Segment A with Segment B/C. The first route employed Segment A with furan moiety as masked maleic anhydride. In the second route, maleic anhydride as Segment A was directly used to accomplish the improved synthesis. Removal of the silyl protecting group with pyridinium poly(hydrogen fluoride) (HF-Py) at the final step completed the total synthesis of tautomycin.
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