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Asymmetric Stereodivergent Strategy Towards Aminocyclitols
Author(s) -
Trost Barry M.,
Malhotra Sushant
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402175
Subject(s) - desymmetrization , diastereomer , stereochemistry , chemistry , enantioselective synthesis , combinatorial chemistry , computer science , catalysis , organic chemistry
A concise asymmetric synthesis of aminocyclitols, such as diastereomeric 2‐deoxystreptamine analogues and conduramine A, is described. The Pd‐catalyzed asymmetric desymmetrization of meso 1,4‐dibenzolate enables the synthesis of highly oxidized cyclohexane architectures. These scaffolds can potentially be used to access new aminoglycoside antibiotics and enantiomerically pure α‐glucosidase inhibitors.