Expeditious synthesis of enantiopure symmetrical macroheterocycles by ring-closing metathesis of ether and tether-linked 1,2-O-isopropylidenefuranosides.
Bis-olefinic symmetrical carbohydrate derivatives were prepared by joining two 1,2-O-isopropylidenefuranose units either through an ether linkage or by a tether of variable size. The ring-closing metathesis (RCM) of these substrates using Grubbs' first-generation catalyst led to the synthesis of enantiopure symmetrical macroheterocycles containing nine- to twenty-five-membered rings fused to the 1,2-O-isopropylidenefuranose ring.
Biswas
Goutam
G
Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata 700032, India.
Sengupta
Jhimli
J
Nath
Madhumita
M
Bhattacharjya
Anup
A
D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010429:Pentoses / Q000737:chemistry; D013237:Stereoisomerism
D004987:Ethers; D006571:Heterocyclic Compounds; D010429:Pentoses