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Arch Pharm (Weinheim). 2012 Sep;345(9):677-86. doi: 10.1002/ardp.201200101. Epub 2012 Jul 4.

1,2,4-trisubstituted cyclopentanes as platforms for diversity.

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1
Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University School of Pharmacy and Pharmaceutical Sciences, West Lafayette, IN, USA.

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.

PMID:
22760821
DOI:
10.1002/ardp.201200101
[Indexed for MEDLINE]
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