A stereoselective cyclization to carbafuranose derivatives starting from 1,4-bis-epoxides.
[reactions: see text] A concise synthesis of highly functionalized cyclopentane derivatives via a Brook rearrangement mediated stereoselective linchpin cyclization reaction involving tert-butyldimethylsilyl-1,3-dithianyllithium and homochiral 1,4-bis-epoxides is described.
Leung
Leo M H
LM
School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom.
Boydell
A James
AJ
Gibson
Vicky
V
Light
Mark E
ME
Linclau
Bruno
B
D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010429:Pentoses / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D009942:Organometallic Compounds; D010429:Pentoses; D012821:Silanes; D008094:Lithium