TY - JOUR
T1 - Synthesis and conformational analysis of a bridged anabasine and related compounds. A nuclear magnetic resonance spectroscopy and molecular modeling study.
AU - Prokai-Tatrai, Katalin
AU - Zoltewicz, John A.
AU - Kem, William R.
N1 - Funding Information:
This work was supported by Taiho Pharmacetical Co., Tokyo, Japan. The authors thank Mr. Craig Porter for his assistance with the CaCheTM Worksystem, and for obtaining the 500 MHz NMR spectra.
PY - 1994
Y1 - 1994
N2 - The synthesis and conformational analysis of a "bridged" anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.
AB - The synthesis and conformational analysis of a "bridged" anabasine, 5,8,9,10,11,11a-hexahydro-6H-pyrido[2,1-f][1,6] naphthyridine (5), and related compounds are reported. Conformational assignments were made using NMR data (including coupling constants, homonuclear Overhauser effects, and 2D correlations) and the results of molecular mechanics (MM2) calculations. The tricyclic compounds have trans-quinolizidine ring fusion with a chair-shaped piperidine ring. The center ring shows a half-chair conformation for the title compound, and a half-boat shape for its 6-oxo derivative. Calculated vicinal coupling constants are in good agreement with those obtained experimentally.
KW - Bridged anabasine
KW - Conformational analysis
KW - Molecular mechanics.
KW - Nuclear Overhauser enhancement
UR - http://www.scopus.com/inward/record.url?scp=0028001571&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)89606-X
DO - 10.1016/S0040-4020(01)89606-X
M3 - Article
AN - SCOPUS:0028001571
SN - 0040-4020
VL - 50
SP - 9909
EP - 9918
JO - Tetrahedron
JF - Tetrahedron
IS - 33
ER -