A practical and improved process for the synthesis of Hagen’s gland lactones by catalytic hydro-deiodination

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)