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Total Synthesis of (±)-Merrilactone A via Catalytic Nazarov Cyclization

2006; American Chemical Society; Volume: 129; Issue: 3 Linguagem: Inglês

10.1021/ja068150i

1943-2984

Wei He, Jie Huang, Xiufeng Sun, Alison J. Frontier,

Plant-derived Lignans Synthesis and Bioactivity

The total synthesis of merrilactone A (a neurotrophic agent) has been achieved. In the approach reported, simultaneous creation of the C-4 and C-5 stereocenters was accomplished stereospecifically using an unprecedented variant of the Nazarov cyclization. Additional studies focused upon this Lewis acid-catalyzed cyclization of a silyloxyfuran-containing intermediate are presented.