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Absolute Stereochemical Assignment of SCH 71450, a Selective Dopamine D 4 Receptor Antagonist, Through Enantioselective Epimer Synthesis
Author(s) -
Wu HsinPei,
Lu TaiNi,
Hsu NaiYun,
Chang CheChien
Publication year - 2013
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.201300072
Subject(s) - chemistry , enantioselective synthesis , stereochemistry , substituent , absolute configuration , epimer , moiety , stereoselectivity , imine , asymmetric carbon , derivative (finance) , glycosylation , organic chemistry , catalysis , optically active , financial economics , economics , biochemistry
The absolute stereochemical assignment of SCH 71450, a selective dopamine D 4 receptor antagonist, has been successfully confirmed through enantioselective epimer synthesis. An allyl substituent on the p ‐hydroxybenzyl group was demonstrated to be an appropriate protecting group for Noyori Ru‐catalyzed asymmetric transfer hydrogenation of the imine derivative. The construction of the sugar moiety involved a β‐glycosylation reaction assisted by neighboring group participation. By comparison with literature data, the absolute stereochemistry at the C‐1 carbon on the tetrahydroisoquinoline core has been assigned the S configuration.