657397-03-0Relevant articles and documents
Enzymatic resolution of aminocyclopentenols as precursors to D- and L- carbocyclic nucleosides
Mulvihill,Gage,Miller
, p. 3357 - 3363 (1998)
Racemic cis-4-aminocyclopent-2-en-1-ols were synthesized in three steps utilizing hetero Diels-Alder chemistry. Starting from suitably protected hydroxylamines, oxidization with sodium periodate and trapping with cyclopentadiene afforded cycloadducts (±)-5a-d. The N-O bond of the cycloadducts was reduced with Mo(CO)6 to afford (±)-cis-4-aminocyclopent- 2-en-1-ols (±)-6a-d. These compounds, or their corresponding acetates, were kinetically resolved by enzymatic acetylation of hydrolysis, respectively. Enzymatic acetylation of cis-N-(benzylcarbamoyl)-4-aminocylopent-2-enol [(±)-6a] with Candida antarctica B lipase and Pseudomonas species lipase gave the corresponding acetate (-)-7a in 90% and 92% ee, respectively, after 40% conversion. Enzymatic hydrolysis of cis-N-acetyl-4-aminocyclopent-2-enol 1-O-acetate (±)-7d with electric eel acetylcholine esterase was successful in providing both cis-N-acetyl-4-aminocyclopent-2-enols (+)-6d and (+)-7d in 92% ee (99% ee after a single recrystallizaton) after 40% conversion. Further synthetic transformation of these resolved synthetic building blocks and derivatives are also reported.
Chemoenzymatic asymmetric total synthesis of phosphodiesterase inhibitors: Preparation of a polycyclic pyrazolo[3,4-d]pyrimidine from an acylnitroso Diels-Alder cycloadduct-derived aminocyclopentenol
Jiang, May Xiao-Wu,Warshakoon, Namal C.,Miller, Marvin J.
, p. 2824 - 2827 (2007/10/03)
(Chemical Equation Presented) Enzymatic resolution of Boc-protected 4-aminocyclopenten1-ol 4c gave both enantiomers 5c and 6c in high ee. Boc removal and separate condensation with chloropyrazolopyrimidine 18 provided elaborated 1,4-aminocyclopentenol derivatives 20 and 26, respectively. Separate treatment of 20 and 26 with Pd(0) under basic conditions induced cyclization to unsaturated polycycles 22 and 27, which, upon catalytic hydrogenation, were transformed to new cyclopentane-containing pyrazolopyrimidines 24 and 28, analogues of recently described novel phosphodiesterase inhibitors.
IMPROVEMENTS IN PHARMACEUTICALLY USEFUL COMPOUNDS
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Page 45-46, (2010/11/30)
A compound of formula (I) or (II): wherein A is hydrogen or CR1R2; Y and Z are each, independently, hydrogen or a halogen;X is -NR4R5, or R7; R1 is hydrogen, or a substituted or unsubstituted alkyl or alkenyl group containing 1-4 carbon atoms; when X is -NR4R5, R2 is a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1-12 carbon atoms; when X is R7, R2 is an unsubstituted alkyl, alkenyl or alkynyl group, or a substituted or unsubstituted aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1-12 carbon atoms; R3 is a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1-12 carbon atoms; R4 is hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1-12 carbon atoms, -COOR8, or -COR8; R5 is hydrogen, or a substituted or unsubstituted alkyl or alkenyl group containing 1-5 carbon atoms; R7 is an unsubstituted alkyl, alkenyl, or alkynyl group, that contains 1-4 carbon atoms; and, R8 is an unsubstituted or halo-substituted alkyl, aryl, or aralkyl group, that contains 1-12 carbon atoms.
Synthesis of 4-azacyclopent-2-enones and 5,5-dialkyl-4-azacyclopent-2- enones
Dauvergne, Jér?me,Happe, Alan M.,Jadhav, Vasudev,Justice, David,Matos, Marie-Christine,McCormack, Peter J.,Pitts, Michael R.,Roberts, Stanley M.,Singh, Sanjay K.,Snape, Timothy J.,Whittall, John
, p. 2559 - 2567 (2007/10/03)
Three different methods are reported for the preparation of 4-azacyclo-2-enones 1, two of which allow the preparation of the compounds in optically active form. In addition, a facile route to 4-aza-5,5- dimethylcyclopent-2-enones 2 is disclosed.
