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Stereoselective Desymmetrization of 2,2‐Bishydroxymethyl‐1‐tetralones by Iodocyclization, Synthesis of Novel Enantiopure [6.6.5] Tricyclic Framework and Chemoenzymatic Diversity Generation
Author(s) -
Mahapatra Tridib,
Javendu,
Nanda Samik
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100088
Subject(s) - enantiopure drug , chemistry , stereoselectivity , desymmetrization , tricyclic , kinetic resolution , tetralones , stereochemistry , aspergillus niger , organic chemistry , enantioselective synthesis , catalysis , biochemistry
Stereoselective halocyclization of pro‐chiral 2,2‐bishydroxymethyl‐1‐tetralone derivatives with N ‐halosuccinamides afforded an interesting tricyclic scaffold found in many naturally occurring hasubanan alkaloids. Enantiopure tricyclic scaffolds are synthesized by using enzymatic kinetic resolution (EKR) of the parent racemic compound. Microbial ketoreductase ( Geotrichum candidum , Aspergillus niger and Candida parapsilosis ) mediated stereoselective reduction reactions have been successfully employed to these enantiopure tricyclic scaffolds which, followed by functional group manipulation, provides novel cyclic frameworks.