Papers by Franco Fernández
Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 2008
The first members of a new family of heterocarbobicyclic nucleoside analogues have been synthesiz... more The first members of a new family of heterocarbobicyclic nucleoside analogues have been synthesized from the cis/trans mixture of (4-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl)methanols cis/trans-7. The separation of cis and trans intermediates during preparation of the 6-chloropurine derivatives allowed separate preparation of the purine heterocarbanucleosides cis-10 and trans-11, from which cis-(12-14) and trans-(16-18) were obtained by replacement of the 6-chloro substituent with amino, hydroxy and cyclopropylamino groups. Additionally, the 6-phenyl-purinyl analogues cis-15 and trans-19 were prepared from cis-10 and trans-11 using Suzuki-Miyaura methodology.
Tetrahedron, 2002
(±)-c-4-Amino-r-1,t-2,c-3-cyclopentanetrimethanol (4) was synthesized from previously reported (±... more (±)-c-4-Amino-r-1,t-2,c-3-cyclopentanetrimethanol (4) was synthesized from previously reported (±)-c-4,t-5-bis(benzoyloxymethyl)-r-1,c-3-cyclopentanedicarboxylic anhydride by methanolysis (which selectively esterified the less hindered carboxyl), oxidative degradation of the other to an amino group, and DIBAL-H reduction. Amino alcohol 4 was then converted into (±)-c-4-[(5-amino-6-chloropyrimidin-4-yl)amino]-r-1,t-2,c-3-cyclopentanetrimethanol, which was used for synthesis of 8-azapurine arabino-carbocyclic nucleoside analogues. Two N,N′-dicyclopentanylurea derivatives obtained as side products of the synthesis of 4 are also described.Graphic
ChemInform, 2010
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Nucleosides, Nucleotides and Nucleic Acids, 1995
The aminoalcohol 4 has been converted into carbocyclic nucleoside analogues 2 and 3.
Nucleosides, Nucleotides and Nucleic Acids, 2001
Several cyclobutyladenine and analogous carbonucleosides were synthesized from 1R-alpha-pinene an... more Several cyclobutyladenine and analogous carbonucleosides were synthesized from 1R-alpha-pinene and their anti-viral activity was tested. One of them (3e) showed interesting selectivity against both TK+ and TK- VZV.
Nucleosides, Nucleotides and Nucleic Acids, 2001
The synthesis of some 9-(2-cyclobutylethyl)guanine derivatives and analogous carbonucleosides fro... more The synthesis of some 9-(2-cyclobutylethyl)guanine derivatives and analogous carbonucleosides from 1S-alpha-pinene is here presented. None of them showed detectable selectivity when assayed in the performed anti-viral tests.
Chemical and Pharmaceutical Bulletin, 1999
Synthesis, 2003
Reaction of hydrazine with exo,exo-3-hydroxymethylene-5,6-isopropylidenedioxybicyclo[2.2.1]heptan... more Reaction of hydrazine with exo,exo-3-hydroxymethylene-5,6-isopropylidenedioxybicyclo[2.2.1]heptan-2-one led to norbornenepyrazole 7, which was converted to its 1-and 2-alkyl derivatives. Deprotection of the vicinal hydroxyls, oxidative cleavage of the resulting glycol and reduction of the dialdehyde so obtained afforded 1-and 2-alkylcyclopenta[c]pyrazole-4,6-dimethanols, which are of interest as intermediates in the preparation of nucleoside analogues derived from 1H-and 2H-cyclopenta[c]pyrazole.
Organic Preparations and Procedures International, 1992
European Journal of Medicinal Chemistry, 1987
This article describes the synthesis of a series of butyrophenone analogues in which the propyl c... more This article describes the synthesis of a series of butyrophenone analogues in which the propyl chain is partially included in a cyclopentane ring. These trans-(2-aminomethyl)cyclopentyl aryl ketones are obtained by reacting (2-bromomethyl)cyclopentyl phenyl ketone or (2-...
Synthesis, 2000
The title amino alcohols 6 and 7, which are of interest as intermediates in the synthesis of carb... more The title amino alcohols 6 and 7, which are of interest as intermediates in the synthesis of carbocyclic analogs of nucleosides, were synthesized from (+)-nopinone (8). Ring opening of a-isonitrosonopinone leads to a cyanoester which can be directly reduced to 6. Alternatively, a longer route from the lactam 12, one of the Beckmann rearrangement products of 8, leads also to 6, in a higher overall yield. Besides this the isomeric lactam 13 was transformed, upon hydrolytic opening, oxidative degradation of the lateral chain and reduction, into 7.
ChemInform, 2010
Synthesis of (1'S,3'R)-3-(3'-Amino-2',2'-dimethylcyclobutyl)propan-1-ol from (-)-β-Pinene.-The ti... more Synthesis of (1'S,3'R)-3-(3'-Amino-2',2'-dimethylcyclobutyl)propan-1-ol from (-)-β-Pinene.-The title compound (XI) represents a useful intermediate in the synthesis of carbocyclic nucleoside analogues.-(BLANCO,
ChemInform, 2010
Syntheses of Chiral Menthyl and Neomenthyl Sulfides, Sulfoxides and Sulfones.-Reductive cleavage ... more Syntheses of Chiral Menthyl and Neomenthyl Sulfides, Sulfoxides and Sulfones.-Reductive cleavage of the readily obtained dithioacetal (III) of menthone gives an irresolvable mixtures of epimeric thiols (IV) and (V) in almost quantitative yield. Permanganate oxidation of therefrom derived dinitrophenyl sulfide derivatives provides the corresponding sulfoxides and sulfones. The resolution of the epimeric sulfones by chromatography as well as recrystallization fails.-(BLANCO,
Tetrahedron: Asymmetry, 2005
Abstract (−)-(1 R ,3 S )-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(1 R ,3 S )-3-ami... more Abstract (−)-(1 R ,3 S )-3-Amino-2,2-dimethylcyclobutanecarboxylic acid and (+)-(1 R ,3 S )-3-amino-2,2-dimethylcyclobutylmethanol, which can be used to prepare enantiopure oligopeptides and cyclobutane-based carbocyclic nucleosides, were synthesized from (+)-(1 R )-α-pinene.
ChemInform, 2010
Synthesis and Pharmacological Screening of Some N-(4-Substitutedpiperazin-1-ylalkyl)-3,4-pyrroled... more Synthesis and Pharmacological Screening of Some N-(4-Substitutedpiperazin-1-ylalkyl)-3,4-pyrroledicarboximides.-Novel compounds (I) with analgesic activity are prepared. The analgesic activity is found to be higher in compounds with high lipophilicity.-(MALINKA, WIESLAW;
Synthesis, 2005
ABSTRACT The first members of a new class of carbocyclic nucleoside analogs were synthesized via ... more ABSTRACT The first members of a new class of carbocyclic nucleoside analogs were synthesized via key intermediate (+/-)-(cis)-2-bencyleyclopenta[c]pyrazole-4,6-di methanol, which was obtained from the easily prepared starting compound (+/-)-(exo,exo)-5,6-isopropylidenedioxy-4,5,6,7-tetrahydro-4,7-methano-2 H-indazole by a reaction sequence in which the key step was a one-pot oxidative cleavage of glycol 9 and reduction of the resulting dialdehyde with NaBH4. Purine moieties were coupled by nucleophilic displacement following mesylation of the latter. The new compounds 15 and 17 are active against cytomagalovirus and varicella-zoster virus at subcytotoxical concentrations.
Synthesis, 2006
Two new 6-aryl-substituted 1¢(N)-homocarbanucleosides were prepared by Suzuki-Miyaura reactions o... more Two new 6-aryl-substituted 1¢(N)-homocarbanucleosides were prepared by Suzuki-Miyaura reactions of the protected 6-halopurine derivatives with phenylboronic acids. Additionally, 1¢(N)-homocarbanucleosides of 6-chloropurine, 2-amino-6-chloropurine and 3-benzoyluracil were prepared by Mitsunobu reaction with a protected diol. From the uracil derivative, the corresponding 5-bromo-and 5-iodouracil compounds were also obtained.
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Papers by Franco Fernández