Premium
The Synthesis of Cyclophellitol‐Aziridine and Its Configurational and Functional Isomers
Author(s) -
Jiang Jianbing,
Artola Marta,
Beenakker Thomas J. M.,
Schröder Sybrin P.,
Petracca Rita,
de Boer Casper,
Aerts Johannes M. F. G.,
van der Marel Gijsbert A.,
Codée Jeroen D. C.,
Overkleeft Herman S.
Publication year - 2016
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.201600472
Subject(s) - aziridine , chemistry , intramolecular force , moiety , epoxide , stereochemistry , combinatorial chemistry , organic chemistry , ring (chemistry) , catalysis
Cyclophellitol and cyclophellitol‐aziridine are potent, mechanism‐based and irreversible retaining β‐glucosidase inhibitors. We have become interested in these configurational β‐glucoside analogues as they proved to be a highly suitable starting point for the development of activity‐based glycosidase probes. In this review, we provide an overview of the cyclophellitol‐aziridine synthesis reported in the literature. Two conceptually different strategies for the introduction of the aziridine moiety have been used, one starting from the inverted epoxide and one with intramolecular iodocyclisation from a homo‐allylic alcohol as the key step. These are discussed in this microreview, and their application in the synthesis of configurational and functional cyclophellitol‐aziridine isomers is presented as well.