The stereoselective generation of ester enolates
1975; Elsevier BV; Volume: 16; Issue: 46 Linguagem: Inglês
10.1016/s0040-4039(00)91213-9
ISSN1873-3581
AutoresRobert E. Ireland, Alvin K. Willard,
Tópico(s)Chemical Reactions and Isotopes
ResumoA synthetic approach to pordamacrine A that features two key transformations is discussed. The first transformation applies an Ireland-Claisen rearrangement to establish sterically congested vicinal carbon centers. Although a hard enolization technique for accessing the silyl ketene acetal failed, a soft enolization, boron-based reaction was highly successful. The second step involves a proposed cascade palladium-catalyzed biscyclization to construct two carbocycles of the natural product. The overall strategy is presented, demonstrating the challenges of the cyclization events in this complex setting.
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