Intramolecular aldol cyclization of L-lyxo-hexos-5-ulose derivatives: a new diastereoselective synthesis of D-chiro-inositol

The DBU-promoted intramolecular aldol condensation of two partially protected l-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl b-d-galactopyranoside, takes place with fairly good yield and complete diastereoselectivity to give 2l-(2,3,6/4,5)-pentahydroxycyclohexanone derivatives, 10 and 11. The stereoselective reduction of inosose 10 with sodium triacetoxyborohydride leads, after catalytic debenzylation, to d-chiro-inositol (1), while the sodium borohydride reduction furnishes, with opposite stereoselectivity, a derivative of allo-inositol

A new highly stereoselective synthesis of epi-inositol from D-galactose

The inosose derivative 3 was obtained with high stereoselectivity by intramolecular aldol condensation of the aldohexos-5-ulose derivative 2, and it was selectively reduced and debenzylated to give epi-inositol in high yield. The stereochemistry and the preferred conformations of compounds 3–7 were determined through 1D and 2D NMR experiments

Syntheses of Isoxazoline-Carbocyclic Nucleosides and Their Antiviral Evaluation: A Standard Protocol

The current synthesis of racemic purine and pyrimidine isoxazoline-carbocyclic nucleosides is reported, detailing the key-steps for standard and reliable preparations. Improved yields were obtained by the proper tuning of the single synthetic steps, opening the way for the preparation of a variety of novel compounds. Some of the obtained compounds were also evaluated against a wide variety of DNA and RNA viruses including HIV. No specific antiviral activity was observed in the cases at hand. Novel compounds were prepared for future biological tests