Advances towards the synthesis and characterization of five-membered cyclic alcohols and ketones

This study reports the synthesis of a group of differently substituted cyclopentane derivatives, which are of interest as intermediates in the preparation of compounds with potential pharmacological activities, such as the carbocyclic analogues of nucleosides. The azide group in the azido alcohol derivatives of type 4 was easily reduced by way of a Staudinger reaction and protected in situ as the Boc-amino derivatives 5. Subsequent oxidation with CrO3 gave the corresponding ketones 6. Similarly, conversion of 4b into the phthalimide derivative with the hydroxyl group protected as acetate allowed us to obtain the oxo derivative 11. All the new prepared compounds were fully characterised by NMR spectroscopy and mass spectrometry.

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