A short dipolar cycloaddition approach to γ-lactam alkaloids from Cynometra hankei

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3915-3918

  Fishwick, Colin W G ^a   Foster, Richard J ^a   Carr, Robin E ^b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ANALGESIC AGENT; CYNOMETRINE; GAMMA LACTAM DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; TREE;

EID: 0030014602     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00688-0     Document Type: Article

References (12)

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2. Waterman, P.G.; Faulkner, D.F. Phytochemistry 1981, 20, 2765. Monseur, X.; Khuong-Huu, F.; Ratle, G.; Lukacs, G.: Goutarel, R. Tetrahedron Lett. 1973, 1757.
3. Hennart, J.A.A. Ger Offen. 2,307,867 (Chem. Abs. 1974, 80, 19535b), Omnium Chimique S.A. Belg. 780, 935 (Chem. Abs. 1973, 78, 133642t).
4. Hennart, J.A.A. Ger Offen. 2,307,867 (Chem. Abs. 1974, 80, 19535b), Omnium Chimique S.A. Belg. 780, 935 (Chem. Abs. 1973, 78, 133642t).
5. Fishwick, C.W.G.; Foster, R.J: Carr, R.E. Tetrahedron Lett. 1995, 36, 9409.
6. Khuong-Huu, F.; Benechie, M.; Tchissambou, L. Tetrahedron, 1982, 38, 2687.
7. Fishwick, C.W.G.; Foster, R.J: Carr, R.E. Tetrahedron Lett. 1996, 37, 711.
8. Molecular models were constructed on a Silicon Graphics Indigo using MacroModel v3.0, developed by Professor W.C. Still. All models were fully optimised using the AMI Hamiltonian in MOPAC v6.0 running on a Silicon Graphics Challenge eight processor parallel computer. Molecular oribital energies, coefficients, and electronic dipole moments were obtained from the AMI calculations. Interaction energies were calculated using the expression derived by Salem with a value of 5.0 for the resonance overlap integral for carbon-carbon bond formation, βc-c , at 2.0 Å, see; Salem, L. J. Am. Chem. Soc. 1968, 90, 543.
9. Buchanan, R.M.; Richardson, J.F. Inorg. Chem. 1994, 33, 2376.
10. The stereochemical-directing effects of other azoles upon reductions of proximal carbonyl groups has been noted, see: Thieme, P.C.: Sauter, H.: Reissenweber, E. Chem. Ber., 1988, 121, 1059.
11. 3), 5.23 (1H, d, J = 3.0Hz, H-11), 6.09 (1H, s, H-5), 7.19-7.38 (6H, m, Ar-H). All new compounds gave satisfactory spectroscopic and analytical data consistent with their proposed structures. Full experimental details will be published elsewhere.
12. Gimmett, M.R. in: Adv. Het. Chem.; Eds. Katritzky, A.R.: Boulton, A.J. Academic Press, 1970, 12, 103-183.