In:
European Journal of Organic Chemistry, Wiley, Vol. 2018, No. 47 ( 2018-12-19), p. 6800-6808
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 – 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.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2018.47
DOI:
10.1002/ejoc.201801318
Language:
English
Publisher:
Wiley
Publication Date:
2018
detail.hit.zdb_id:
1475010-7