Stereoselective synthesis of gamma-lactone fused cyclopentanoids

Gumus A., TANYELİ C.

TETRAHEDRON-ASYMMETRY, vol.23, pp.1405-1409, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23
  • Publication Date: 2012
  • Doi Number: 10.1016/j.tetasy.2012.09.010
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1405-1409
  • Van Yüzüncü Yıl University Affiliated: Yes

Abstract

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. (C) 2012 Elsevier Ltd. All rights reserved.