Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of sch …

…, DA Cogan, GE Hofilena, AH Hoveyda

Index: Xu, Zhongmin; Johannes, Charles W.; Houri, Ahmad F.; La, Daniel S.; Cogan, Derek A.; Hofilena, Gloria E.; Hoveyda, Amir H. Journal of the American Chemical Society, 1997 , vol. 119, # 43 p. 10302 - 10316

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Citation Number: 159

Abstract

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 ...