Synthesis of Highly Functionalized
Cyclopentanes as Precursors of Hydroxylated Azidocarbonucleosides

Loránd Kiss; Enikö Forró; Reijo Sillanpää; Ferenc Fülöp

doi:10.1055/s-0029-1217088

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Synthesis 2010(1): 153-160
DOI: 10.1055/s-0029-1217088

PAPER

Synthesis of Highly Functionalized Cyclopentanes as Precursors of Hydroxylated Azidocarbonucleosides

Loránd Kiss^a, Enikö Forró^a, Reijo Sillanpää^c, Ferenc Fülöp*^a,b
^a Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
^b Research Group of Stereochemistry of the Hungarian Academy of Sciences, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary
Fax: 0036(62)545705; e-Mail: fulop@pharm.u-szeged.hu;
^c Department of Chemistry, University of Jyväskylä, 40351 Jyväskylä, Finland

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Publication History

Received 8 July 2009
Publication Date:
26 October 2009 (online)

Abstract
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Abstract

Regio- and stereoisomers of functionalized azido amino alcohols with a cyclopentane skeleton were synthesized in enantiomerically pure forms. Enzymatic ring cleavage of racemic 2-azabicyclo[2.2.1]hept-5-en-3-one gave the corresponding amino acid and one enantiomer of the lactam stereospecifically. These were protected by esterification and carbamoylation, and then epoxidized. The resulting oxiranes underwent cleavage by sodium azide with complementary stereoselectivities. The regioisomeric products were easily separated by crystallization or column chromatography.

Key words

amino acids - carbocycles - nucleosides - amino alcohols - enzymes

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