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Recherches dans la série des cyclitols XLII. Synthèses de cyclitols tout‐cis dérivés du cyclopentane; préparation des cyclopentane‐tétrol et ‐ pentol tout‐cis
Author(s) -
Cocu F. G.,
Posternak Th.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540619
Subject(s) - cyclopentane , chemistry , stereochemistry , medicinal chemistry
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.