Stereoselective synthesis of gamma-lactone fused cyclopentanoids

Date

2012-10-15

Author

Gumus, Aysegul
Tanyeli, Cihangir

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The stereoselective synthesis of gamma-lactone fused cyclopentanoids applying chemoenzymatic methods is described. rac-2-Hydroxymethyl-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-ene and rac-2-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene were successfully resolved by Candida rugosa lipase (CRL), to afford enantiomerically enriched products with an ee of 94 and 97%, respectively. The enantiomerically enriched acetates were then subjected to ruthenium and/or cerium catalyzed oxidation to afford alpha-diketones and subsequent alkaline H2O2 mediated oxidative cleavage reaction of alpha-diketones, followed by CH2N2 esterification, gave enantiomerically enriched gamma-lactone fused cyclopentanoids with known absolute configurations.

Subject Keywords

Stereocontrolled total synthesis, Hexachloronorbornadiene derivatives, Alpha-diketones, Resolution, Norbornadiene, Cyclization, Annulation, System, Acids

URI

https://hdl.handle.net/11511/47721

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2012.09.010

Collections

Department of Chemistry, Article

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Citation Formats

A. Gumus and C. Tanyeli, “Stereoselective synthesis of gamma-lactone fused cyclopentanoids,” TETRAHEDRON-ASYMMETRY, pp. 1405–1409, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47721.