Portal de Periódicos da CAPES

Stereoselective Synthesis of Tetrahydrofuran Lignans via BF 3 ·OEt 2 -Promoted Reductive Deoxygenation/Epimerization of Cyclic Hemiketal: Synthesis of (−)-Odoratisol C, (−)-Futokadsurin A, (−)-Veraguensin, (+)-Fragransin A 2 , (+)-Galbelgin, and (+)-Talaumidin

2007; American Chemical Society; Volume: 9; Issue: 20 Linguagem: Inglês

10.1021/ol7016388

1523-7060

Hyoungsu Kim, Ceshea M. Wooten, Yongho Park, Jiyong Hong,

Phytochemistry and Biological Activities

A versatile route to the synthesis of 2,5-diaryl-3,4-dimethyltetrahydrofuran lignans, (−)-odoratisol C (1), (−)-futokadsurin A (2), (−)-veraguensin (3), (+)-fragransin A2 (4), (+)-galbelgin (5), and (+)-talaumidin (6), is described. Central to the synthesis of the lignans is BF3·OEt2-promoted deoxygenation/epimerization of the hemiketal 9a followed by stereoselective reduction of the oxocarbenium ion intermediates 8a,b.