A novel dioxabicyclo[3.3.1]nonane, a key intermediate in the synthesis of erythronolide B seco-acid.
In the title compound, (1R,4S,5R,6R,8R)-1-ethyl-4,6,8-trimethyl-2,9-dioxabicyclo[3.3.1]++ +nonan-6-yl 1-imidazolecarboxylate, C16H24N2O4, the 2,9-dioxabicyclo[3.3.1]nonane ring system assumes a double-chair conformation. Bond angles around the ring are enlarged compared to normal tetrahedral values to alleviate some of the overcrowding which results from close intramolecular H...H and C...C contacts. The N-imidazolylcarbonyloxy group is nearly planar with dihedral angles of 5.2 (2) and 6.0 (2) degrees between the imidazole and carbonyl groups for molecules 1 and 2, respectively.
Lynch
V M
VM
Department of Chemistry and Biochemistry, University of Texas at Austin 78712.
Lee
W C
WC
Martin
S F
SF
Davis
B E
BE
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic; D018360:Crystallography, X-Ray; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis*; D015394:Molecular Structure
C090574:1-ethyl-4,6,8-trimethyl-2,9-dioxabicyclo(3.3.1)nonan-6-yl 1-imidazolecarboxylate; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007093:Imidazoles; C038315:erythronolide B; D004917:Erythromycin