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Enantioselective Total Synthesis of Borrelidin

2003; American Chemical Society; Volume: 125; Issue: 6 Linguagem: Inglês

10.1021/ja028941u

1943-2984

Matthew O. Duffey, Arnaud LeTiran, James P. Morken,

Advanced Synthetic Organic Chemistry

The first total synthesis of the natural product borrelidin is described. The propionate fragment of the molecule was concisely synthesized through catalytic enantioselective reductive aldol reactions, a catalytic Negishi coupling, and a catalytic directed hydrogenation. The propionate segment was then fused to the vinyl iodide fragment through a catalytic Sonogashira coupling. Subsequent catalytic hydrostannylation and catalytic cyanation allowed access to the target structure.