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- Title
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.
- Authors
Dubbu, Sateesh; Bardhan, Anirban; Chennaiah, Ande; Vankar, Yashwant D.
- Abstract
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 –OTBDPS 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. Studies toward synthesis of the 2,3‐dideoxy‐3C‐formyl β‐C‐aryl/alkyl furanosides and 2‐deoxy‐2C‐branched β‐C‐aryl furanoside were described using d‐mannitol derived homoallylic alcohols with carbonyl compounds in the presence of BF3·OEt2 as a catalyst.
- Subjects
PINACOLS; REARRANGEMENTS (Chemistry); FURANOSIDES; ALCOHOL; FUNCTIONAL groups
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 47, p6800
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201801318