170708-57-3Relevant articles and documents
Total synthesis of (+)-tautomycin
Tsuboi, Katsunori,Ichikawa, Yoshiyasu,Jiang, Yimin,Naganawa, Atsushi,Isobe, Minoru
, p. 5123 - 5142 (2007/10/03)
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 baron trifluoride etherate (BF3·OEt2). Two routes have been developed in esterification of Segment A with Segment BIG. 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.