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A Divergent Synthesis of l ‐ arabino ‐ and d ‐ xylo ‐Configured Cyclophellitol Epoxides and Aziridines
Author(s) -
Schröder Sybrin P.,
Petracca Rita,
Minnee Hugo,
Artola Marta,
Aerts Johannes M. F. G.,
Codée Jeroen D. C.,
van der Marel Gijsbert A.,
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.201600983
Subject(s) - chemistry , aziridine , stereochemistry , epoxide , cyclitol , enantioselective synthesis , ring closing metathesis , dihydropyran , oxazoline , metathesis , disaccharide , total synthesis , azide , ring (chemistry) , organic chemistry , catalysis , biochemistry , polymerization , polymer , receptor , inositol
A divergent synthesis to eight d ‐ xylo ‐ and l ‐ arabino ‐cyclophellitol and cyclophellitol aziridine derivatives is described. The syntheses start from d ‐xylose and feature asymmetric allylation followed by ring‐closing metathesis as key steps. Reaction of the cyclohexenes with methyl(trifluoromethyl)dioxirane yielded the title epoxides. The aziridines were prepared either from the epimeric epoxides or by direct aziridination of the cyclohexenes. Finally, beta‐xylosylation of 2,3‐di‐ O ‐benzyl‐ xylo ‐cyclophellitol yielded the corresponding cyclitol epoxide disaccharide, thereby expanding the utility of our strategy to the synthesis of potential endoglycosidase inhibitors.