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All‐cis cyclitols derived from cyclopentane have been prepared in two ways: (i) by LiAlH4 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.
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Cocu et al. (1971) studied this question.
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