Water → HCID 86736057, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 18.5 g. of the reaction product of part D in 200 ml. of toluene is cooled to -78° C. under a nitrogen atmosphere. Dropwise treatment over 30 min. with 155 ml. of a 0.56 molar solution of diisobutylaluminum hydride and toluene is followed by stirring at -78° C. for an additional 30 min. The resulting mixture is then treated with 45 ml. of water and 70 ml. of tetrahydrofuran, added dropwise. The reaction mixture is then diluted with an additional 300 ml. of toluene and allowed to warm to ambient temperature. Stirring is continued for 2 hrs. at 25° C. The mixture is then filtered through diatomaceous earth. The solids are then washed with benzene and ethyl acetate and the combined filtrate washed with brine, dried over magnesium silfate, and concentrated under reduced pressure to yield crude 3α,5α-dihydroxy-2β-(3α-hydroxy-4-phenyl-trans-1-butenyl)-1α-cyclopentaneacid acetaldehyde γ-lactol, bis(tetrahydropyranol ether). Silica gel TLC R f is 0.55 in ethyl acetate.

Provenance & Evidence