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A Cascade of Prins Reaction and Pinacol‐Type Rearrangement: Access to 2,3‐Dideoxy‐3C‐Formyl β‐ C ‐Aryl/Alkyl Furanosides and 2‐Deoxy‐2C‐Branched β‐ C ‐Aryl Furanoside
Author(s) -
Dubbu Sateesh,
Bardhan Anirban,
Chennaiah Ande,
Vankar Yashwant D.
Publication year - 2018
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.201801318
Subject(s) - chemistry , aryl , moiety , alkyl , pyran , pinacol , stereochemistry , stereoselectivity , cascade reaction , rearrangement reaction , medicinal chemistry , organic chemistry , catalysis
2,3‐Dideoxy‐3C‐formyl β‐ C ‐aryl/alkyl furanosides were synthesized in a stereoselective manner through a cascade of Prins reaction and pinacol‐type rearrangement of an – O TBDPS protected homoallylic alcohol, derived from d ‐mannitol, and various carbonyl compounds. Furthermore, this method was successfully applied to the synthesis of a fused‐bicyclic β‐ C ‐aryl furanoside moiety and a 2,3‐dideoxy‐3C‐methyl β‐ C ‐aryl furanoside which are found in core structures of bioactive molecules. Further, the strategy was extended to a silyl‐Prins reaction for the synthesis of a 2‐deoxy‐2C‐branched β‐ C ‐aryl furanoside.