Paolo Lupattelli

Oxyfunctionalization of steroids by dioxiranes: Site and stereoselective C14 and C17 hydroxylation of pregnane and androstane steroids.

Dimethyldioxirane showed to be site and stereoselective in the CH oxygen insertion at C14 and C17 positions of pregnane and androstane steroids. Fine steric control and evidence for the influence of the carbonyl group on the dioxirane reactivity are reported.

Selective oxidation of diols by H2O2/TS-1 system and by DMDO

Abstract Selective oxidations of secondary hydroxyl groups vs. primary ones in 1,n-diols by TS-1/H2O2 catalitic system and by dimethyldioxirane, new reagents with low environmental pollution, are reported.

Efficient desymmetrization of 1,2 and 1,3 diols by dimethyldioxirane

Abstract Dimethyldioxirane was used to monooxidize 1,2 and 1,3 sec,sec-diols to the corresponding ketoalcohols, exploiting the inhibiting effect of the formed carbonyl group on the course of the process.

Sapogenins and dimethyldioxirane : a new entry to cholestanes functionalized at the side chain

Abstract A new and simple opening of the sapogenin spiroketal side chain by DMDO as oxyfunctionalizing agent, with the aim to get an easy approach to steroidal functionalized side chains from natural compounds available in large amounts, is reported.

A highly regio- and stereoselective C5 oxyfunctionalization of coprostane steroids by dioxiranes: An improved access to progestogen and androgen hormones.

Abstract Coprostane steroids are selectively oxyfunctionalized at C 5 by dimethyldioxirane and methyltrifluoromethyldioxirane to give useful intermediates for bioactive compounds.

Oxidation of uracil derivatives and pyrimidine nucleosides by dimethyldioxirane: A new and mild synthesis of 5,6-oxiranyl-5,6-dihydro and 5,6-dihydroxy-5,6-dihydro-derivatives.

Abstract The oxidation of title substrates with dimethyldioxirane afforded 5,6-oxiranyl-5,6-dihydro and cis - / trans -5,6-disubstituted-5,6-dihydro-derivatives.

Novel chiral calix[4]arenes by direct asymmetric epoxidation reaction.

We report the first asymmetric synthesis of trans optically active (+) C 2 1,3-bisarylepoxide of calix[4]arene in excellent chemical yield and >99% ee, and its enantiospecific conversion to the corresponding bis-dioxolane.

OXIDATION OF 3-ARYLISOCHROMANS BY DIMETHYLDIOXIRANE. AN EASY ROUTE TO SUBSTITUTED 3-ARYLISOCOUMARINS

Abstract The selective oxidation of the two different benzylethereal position of 3-arylisochromans by dimethyldioxirane as a function of different substituents on the aromatic rings was studied. The easy oxidation of these compounds was exploited for a new easy access to substituted 3-arylisocoumarins.

AN EFFICIENT OXYFUNCTIONALISATION BY DIMETHYLDIOXIRANE OF THE BENZYLETHEREAL CARBON OF FLAVONOIDS; A GENERAL AND USEFUL WAY TO ANTHOCYANIDINS

Abstract compounds with flavonoid structure were selectively oxyfunctionalised at the C-2 carbon atom by DMD. The reaction permitted a new route to flavylium salts.

OXYFUNCTIONALISATION OF ACTIVATED METHYLENES BY DIMETHYLDIOXIRANE : AN EASY CONVERSION OF ISOCHROMANS INTO ISOCOUMARINS

Abstract the concerted activating effect of two groups allowed the oxidation of methylene carbons, otherwise almost inert, by dimethyldioxirane. The method permitted an easy oxidation of isochromanes to isocoumarins.