Collect. Czech. Chem. Commun.
1988, 53, 2447-2472
https://doi.org/10.1135/cccc19882447
(1S,7S)-7-Methyl-6,9-diazatricyclo[6,3,0,01,6]tridecane-5,10-dione, a tricyclic spirodilactam containing non-planar amide groups: Synthesis, NMR, crystal structure, absolute configuration, electronic and vibrational circular dichroism
Petr Maloňa, C. L. Barnessb, Miloš Buděšínskýa, Rina K. Dukorc, Dick Van der Helmb, Timothy A. Keiderlingc, Zdena Koblicovád, Františka Pavlíkováe, Miloš Tichýa and Karel Bláhaa
a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Department of Chemistry, University of Oklahoma, Norman, Oklahoma 73019, U.S.A.
c Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60680, U.S.A.
d Research Institute for Pharmacy and Biochemistry, 194 04 Prague 9, Czechoslovakia
e Prague Institute of Chemical Technology, 166 28 Prague 6, Czechoslovakia
Abstract
The title spirocyclic dilactam (1S,7S)-7-methyl-6,9-diazatricyclo[6,3,0,01,6]tridecan-5,10-dione (I), a molecule designed to contain non-planar amide groups, has been synthesized from an optically active precursor of known absolute configuration. The relative and absolute configuration have been determined by X-ray diffraction. The conformation of the compound has been investigated by X-ray, 1H and 13C NMR, electronic and vibrational circular dichroism. The compound possesses moderately non-planar amide groups in the two rings of nonequal geometry. The electronic CD is dominated by inherent chirality of the amide chromophores. The dilactams I and II ((1S,6S)-6-methyl-5,8-diazatricyclo[6,3,0,01,5]undecan-4,9-dione – having five-membered rings) exhibit monosignate amide I VCD and strong VCD bands in the mid-ir region.
