AN IMPROVED SYNTHESIS OF CIS-CIS-TRANS-CYCLOHEXANE-1,2,3-TRIOL

Abstract

Cyclohexerie-3-01 acetate was readily made fro111 cyclohesene and when oxidized, preferably with performic acid, gave 20 to 25y0 yields of partly acylatecl cis-cis-trans-cyclol~exane-1,2,3-triol, but only 1 to 27, oT the cis-trans-cis isomer. The striictures of the three cyclohexa~~e-1,2,3-triols were deduced froin the theory of the Walclen Inversion.

An Efficient and HighlyStereoselective Synthesis ofgala-Quercitolfrom 1,4-Cyclohexadiene

“…The formation of 9 as the sole product may be questioned. A similar elimination reaction was previously observed by treatment of 1,2-dibromocyclohexane with NaOMe to give 3-methoxycyclohexene 17 as the major product in a yield of 60%.…”

Methanolysis of Stereoisomeric Oxides of 3-Methoxycyclohexene

“…The scission of the /3-oxide therefore took place at the same bond as did the scission of the -oxide, demonstrating the unimportance of steric factors in determining the direction of the oxide scissions. This new synthesis of /S-Pyrogallitol (IV) is not of much practical interest since a satisfactory synthesis of this triol has already been reported (1) The conversion of the -oxide to the known triol III and of the 8-oxide to the known stereoisomeric triol IV is conclusive proof that the oxides are stereoisomers. Each of the oxides has been prepared many times over the course of ten years, and each has always exhibited its own constant physical properties, which suggests that the oxides have been satisfactorily separated from each other.…”

A Facile Synthesis of Cyclitols from Cyclohexene

“…The resin was removed by filtration and the filtrate was evaporated to a syrup which was successively acetylated with acetic anhydride and pyridine. 2,3,4/2,2,3,.…”