111612-92-1Relevant articles and documents
Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis, enantioselective total synthesis of Sch 38516 (fluvirucin B1)
Xu, Zhongmin,Johannes, Charles W.,Houri, Ahmad F.,La, Daniel S.,Cogan, Derek A.,Hofilena, Gloria E.,Hoveyda, Amir H.
, p. 10302 - 10316 (2007/10/03)
The first enantioselective total synthesis of antifungal agent Sch 38516, also known as fluvirucin B1, is described. The synthesis includes a convergent asymmetric preparation of amine 17 and acid 18, which are then united to afford diene 62. Metal-catalyzed transformations play a crucial role in the synthesis of the latter moiety. Of particular note are the diastereo- and enantioselective Zr-catalyzed alkylations, a tandem Ti- and Ni-catalyzed process that constitutes a hydrovinylation reaction, and a Ru-catalyzed alcohol oxidation to afford carboxylic acid 18. The requisite carbohydrate 38 is synthesized in a highly diastereo- and enantioselective fashion. Optical purity of the carbohydrate moiety arises from the use of the asymmetric dihydroxylation method of Sharpless; diastereochemical control is achieved through a selective dipolar [3 + 2] cycloaddition with a readily available amine serving as the chiral auxiliary. Union of the appropriately outfitted carbohydrate 71 and diene 62 through an efficient and diastereoselective glycosylation is followed by a remarkably efficient Mo-catalyzed macrocyclization that proceeds readily at room temperature.
The chemistry of O-silylated ketene acetals: Synthesis of N-benzoyl-L-daunosamine
Kita,Itoh,Tamura,Ke,Miki,Tamura
, p. 1446 - 1451 (2007/10/02)
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