Alvaro Somoza

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Nonpolar nucleosides with varying size and shape have been used to study the hydrogen-bonding stabilization and steric effects on RNA interference. The uracil and adenine residues of siRNA guide strands have been replaced by nonpolar isosteres of uracil and adenine and by steric variants. RNAi experiments targeting Renilla luciferase mRNA have shown close(More)
RNA can be chemically synthesized by automated DNA/RNA synthesizers, using protected ribonucleosides activated as phosphoramidites. The efficiency of the synthesis depends greatly on the protecting groups used, especially the protecting group on the 2'-hydroxyl functionality. The strategies employed to place the protecting groups on the desired(More)
[reaction: see text] The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality,(More)
The beta-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.
Exploitation of the beta-hydroxysulfoxide fragment present in a number of enantiomerically pure (SR)- and (SS)-[(p-tolylsulfinyl)methyl]-p-quinols allowed chemo- and stereocontrolled conjugate additions of different organoaluminium reagents to the cyclohexadienone moiety. The same fragment was also shown to act as an efficient chiral masking carbonyl group,(More)
Convergent enantioselective syntheses of angucyclinone-type natural products rubiginones A(2) (2) and C(2) (1) and their 11-methoxy regioisomers 3 a and 3 b have been achieved by using two domino processes from a common enantiomerically pure 1-vinylcyclohexene 4. Key steps in the synthesis of this diene were the stereoselective conjugate addition of AlMe(3)(More)
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