Stereoselective Synthesis of Enantiopure Oxetanes, a Carbohydrate Mimic, an ϵ‐Lactone, and Cyclitols from Biocatalytically Derived β‐Hydroxy Esters as Chiral Precursors. Issue 24 (15th July 2014)

• Record Type: Journal Article
• Authors: Das, Debabrata; Halder, Joydev; Bhuniya, Rajib; Nanda, Samik
• Is Part Of: European journal of organic chemistry. Issue 24(2014)
• Page Start: 5229
• Page End: 5246
• Publication Date: 2014-07-15
• Subjects: Synthesis design -- Asymmetric synthesis -- Carbocycles -- Enzyme catalysis -- Kinetic resolution -- Biological activity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402521
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Biocatalytically derived enantiopure α‐substituted β‐hydroxy esters serve as excellent chirons for the synthesis of a diverse set of structures such as oxetanes, a carbohydrate mimic, an ϵ‐lactone, and carbocyclic and aromatic cyclitols. The starting materials can be easily accessed in enantiopure form from α‐substituted β‐keto esters by biocatalytic reduction with Klebsiella pneumoniae (NBRC 3319). Ring‐closing metathesis (RCM) is one of the key transformations used to create the carbocyclic/heterocyclic frameworks reported in this article. The synthesized cyclitols were screened for their inhibitory effect on α‐ and β‐glucosidases. Abstract : Several enantiopure α‐substituted β‐hydroxy esters have been synthesized using fermenting cells of K . pneumoniae . A distinctive transformation‐based strategy was adopted to access several carbocyclic and heterocyclic scaffolds. The synthesized scaffolds were further diversified by the use of stereoselective dihydroxylation to access cyclitols with glycosidase inhibitory activity.