کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1345155 | 1500346 | 2014 | 4 صفحه PDF | دانلود رایگان |
Catalytic hydro-deiodination has been efficiently employed in the development of a benign process for the synthesis of Hagen’s gland lactones. The process was developed with only two column chromatographic purifications and is applicable for gram scale synthesis. No protecting groups were used in the synthesis which is an added advantage.
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(4R,5R)-4-Hydroxy-5-vinyldihydrofuran-2(3H)-oneC6H8O3[α]D25 = +45.3 (c 0.8, CHCl3)Initial source of chirality: d-glucono-δ-lactoneAbsolute configuration: (4R,5R)
(3aR,5R,6aR)-5-Butyltetrahydrofuro[3,2-b]furan-2(5H)-oneC10H16O3[α]D25 = +48.5 (c 1.0, CHCl3)Initial source of chirality: d-glucono-δ-lactone and diastereoselective iodocyclizationAbsolute configuration: (3aR,5R,6aR)
(3aR,5R,6aR)-5-Hexyltetrahydrofuro[3,2-b]furan-2(5H)-oneC12H20O3[α]D25 = +47.5 (c 1.0, CHCl3)Initial source of chirality: d-glucono-δ-lactone and diastereoselective iodocyclizationAbsolute configuration: (3aR,5R,6aR)
Journal: Tetrahedron: Asymmetry - Volume 25, Issues 13–14, 31 July 2014, Pages 1022–1025