Recherches dans la série des cyclitols XLII. Synthèses de cyclitols <i>tout‐cis</i> dérivés du cyclopentane; préparation des cyclopentane‐tétrol et ‐ pentol <i>tout‐cis</i>

Abstract

Abstract All ‐ cis cyclitols derived from cyclopentane have been prepared in two ways: (i) by LiAlH 4 reduction of all ‐ cis epoxypolyos; (ii) by dimethyl sulfoxide treatment, in the presence of sodium hydrogencarbonate, of brominated derivatives containing a neighbouring benzoyloxy group; under these conditions, the halogen is replaced by a cis ‐oriented hydroxyl group. Thus all ‐ cis cyclopentane‐tetrol and ‐pentol have been prepared; their configuration has been confirmed by NMR. spectroscopy.