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Convenient Synthesis of 3‐Glycosylated Isocoumarins
Author(s) -
Sudarshan Kasireddy,
Aidhen Indrapal Singh
Publication year - 2017
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.201601264
Subject(s) - isocoumarins , isocoumarin , chemistry , ketone , moiety , intramolecular force , pyrone , ring (chemistry) , synthon , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A new route for the synthesis of 3‐substituted and 8‐hydroxy‐3‐substituted isocoumarins was developed by modified Julia olefination for initial C–C bond formation between aldehydes and benzylic sulfones. Palladium‐catalyzed Meinwald rearrangement was used as a key step for the obtainment of ketone intermediates, which – upon base‐promoted intramolecular cyclization – afforded the desired isocoumarins. The developed method paves the way to hitherto unknown 3‐glycosylisocoumarins, in general, and 3‐glucosylisocoumarins, in particular, wherein the glucosyl moiety is attached to the pyrone ring of the isocoumarin framework.