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Stereoselective Synthesis of Enantiopure Oxetanes, a Carbohydrate Mimic, an ϵ‐Lactone, and Cyclitols from Biocatalytically Derived β‐Hydroxy Esters as Chiral Precursors
Author(s) -
Das Debabrata,
Halder Joydev,
Bhuniya Rajib,
Nanda Samik
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402521
Subject(s) - enantiopure drug , chemistry , ring closing metathesis , lactone , stereochemistry , metathesis , cyclitol , stereoselectivity , carbohydrate , ring (chemistry) , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , polymerization , polymer , receptor , inositol
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.