77745-28-9Relevant academic research and scientific papers
Syntheses of carbocyclic aminonucleosides and (-)-epi-4′-carbocyclic puromycin: application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations
Cesario, Cara,Tardibono Jr., Lawrence P.,Miller, Marvin J.
supporting information; experimental part, p. 3053 - 3056 (2010/08/05)
Carbocyclic aminonucleosides and epi-4′-carbocyclic puromycin were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. Pd(0)/InI-mediated allylations of a formyl species were used to install the 4′-hydroxymethyl group. A tethered aminohydroxylation strategy was employed to install the cis-2′,3′-aminoalcohol moiety with complete regio- and diastereocontrol.
A facile synthesis of cis-4-amino-2-cyclopentene-1-methanol, a key intermediate for the synthesis of carbocyclic nucleosides
An, Gwang-Il,Rhee, Hakjune
, p. 65 - 72 (2007/10/03)
A number of carbocyclic nucleosides can be synthesized from (±)-cis-4-amino-2-cyclopentene-1-methanol (3). Carbocyclic amino alcohol 3 is a key intermediate that makes possible the efficient synthesis of the carbocyclic nucleosides. In this study we wish to report an efficient synthesis of carbocyclic amino alcohol 3 from inexpensive and readily available starting material. The synthetic route employed cyclopentadiene (4) as a starting material and proceeded in 38% overall yield through 6 steps involving a hetero Diels-Alder reaction and an aza-Claisen rearrangement.
Carbocyclic Sugar Amines: Synthesis and Stereochemistry of Racemic α- and β-Carbocyclic Ribofuranosylamine, Carbocyclic Lyxofuranosylamine, and Related Compounds
Kam, Bernard L.,Oppenheimer, Norman J.
, p. 3268 - 3272 (2007/10/02)
The facile and stereoselective synthesis of racemic carbocyclic β-ribofuranosylamine, carbocyclic β-lyxofuranosylamine, and related 2,3-cis-dihydroxy carbocyclic pentofuranosylamines is reported.In addition, the synthesis, isolation, and base-catalyzed epimerization of methyl cis-4-aminocyclopent-2-enecarboxylate are described.The epimerization at C(1) followed by stereoselective cis hydroxylation provides for the first time access to the racemic carbocyclic α-pentofuranosylamines.
