title: 1,2,4-trisubstituted cyclopentanes as platforms for diversity.
abstract: Despite their simplicity, relatively few examples of 1,2,4 (1,3,4)-amino-, azido-, and hydroxy-substituted cyclopentanes are reported in the literature. We found that cyclopent-3-en-1-ol can be transformed into a significant variety of compounds of this class by relatively common and efficient synthetic procedures. Stereochemical control of epoxidation of the cyclopentene double bond can be achieved by varying the substitutents at C4. The C4 substituent and epoxide functional group can be converted into a variety of intermediates with differential protection designed for use in applications requiring regiospecific control for further elaboration of the cyclopentane scaffold.
authors: Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University School of Pharmacy and Pharmaceutical Sciences, West Lafayette, IN, USA.
authors: Yousheng
authors: Y
authors: Guan
authors: Caterina
authors: C
authors: Bissantz
authors: Donald E
authors: DE
authors: Bergstrom
authors: Andreas
authors: A
authors: Link
mesh_terms: D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D015394:Molecular Structure; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D054852:Small Molecule Libraries