A facile synthesis of cis-4-amino-2-cyclopentene-1-methanol, a key intermediate for the synthesis of carbocyclic nucleosides.
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.
An
Gwang-il
GI
Department of Chemistry, Hanyang University, Ansan, Kyunggi-do, Korea.
Rhee
Hakjune
H
D003517:Cyclopentanes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis*
C470786:4-amino-2-cyclopentene-1-methanol; D003517:Cyclopentanes; D009705:Nucleosides