An ab initio mechanistic understanding of the regioselective acetylation of 8,11-dihydroxy-pentacyclo[5.4.0.02,6.03,10.0 5,9] undecane-8,11-lactam

Journal of Molecular Structure: THEOCHEM

Volumn 672, Issue 1-3, 2004, Pages 119-125

  Gokul, Vikash ^a   Kruger, Hendrik G ^a   Govender, Thavendran ^a   Fourie, Louis ^b   Power, Trevor D ^c  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

^b NORTH WEST UNIVERSITY   (South Africa)

^c University of Texas Medical Branch School of Medicine   (United States)

Author keywords

Ab initio; Acetylation; Cyclic transition state; Lactam

Indexed keywords

8,11 DIHYDROXYPENTACYCLO[5.4.0.0 2,6 .0 3,10 .0 5,9 ]UNDECANE 8,11 LACTAM; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ACETYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DRUG STRUCTURE; ENANTIOSELECTIVITY; GEOMETRY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; QUANTUM THEORY; REACTION OPTIMIZATION; THERMODYNAMICS;

EID: 1242284109     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2003.11.011     Document Type: Article

References (28)

1. Martins F.J.C., Viljoen A.M., Kruger H.G., Jobert J.A. Tetrahedron. 49:(42):1993;9573.
2. Martins F.J.C., Viljoen A.M., Kruger H.G., Joubert J.A., Wessels P.L. Tetrahedron. 50:(36):1994;10783.
3. Kruger H.G., Martins F.J.C., Viljoen A.M., Boeyens J.C.A., Cook L.M., Levendis D.C. Acta Crystallogr. B52:1996;838.
4. Cookson R.C., Crundwell E., Hill R.R., Hudec J. J. Chem. Soc. 1964;3062.
5. Marchand A.P., Allen R.W. J. Org. Chem. 39:(11):1974;1596.
6. Furniss B.S., Hannaford A.J., Smith P.W.G., Tatchell A.R. Vogel's Textbook of Practical Organic Chemistry. Fifth ed. 1989;Longman, New York.
7. Oliver D.W., Dekker D.G., Snykers F.O., Fourie T.G. J. Med. Chem. 34:1991;851.
8. Oliver D.W., Dekker D.G., Snyckers F.O. Eur. J. Med. Chem. 26:1991;375.
9. Oliver D.W., Dekker D.G., Snyckers F.O. Drug Res. 41:1991;545.
10. Inamoto Y., Aiyami K., Tasaishi N., Fujikura Y.J. J. Med. Chem. 19:1967;536.
11. Inamoto Y., Aiyami K., Kadono T., Makayama H., Takatsuki A., Tumura G. J. Med. Chem. 20:1977;1371.
12. Boeyens J.C.A., Cook L.M., Nelson G.N., Fourie T.G. S. Afr. J. Chem. 47:(2):1994;72.
13. H.G. Kruger, PhD Thesis, Potchefstroom University, Potchefstroom, South Africa, 1996.
14. An undergraduate student first synthesised the mono acetate 5a at 'room temperature' during summer (>25°C). Initially, this result could not be reproduced in winter at 'room temperature' (<25°C), delaying complete elucidation of the structure.
15. Silverstein R.M., Bassler G.C., Morrill T.C. Spectrometric Identification of Organic Compounds. Fifth ed. 1991;Wiley, New York.
16. Kruger H.G. Theochem. 577:2002;281.
17. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A. Jr., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., Pople J.A. GAUSSIAN98, Revision A.9. 1998;Gaussian Inc, Pittsburgh, PA.
18. Power T.D., Sebastian J.F. Tetrahedron. 54:1998;8371.
19. Becke A.D. J. Chem. Phys. 98:1993;5648.
20. Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785.
21. Mielich B., Savin A., Stoll H., Peus H. Chem. Phys. Lett. 157:1989;200.
22. Cartesian coordinates of all optimised structures are available as supplementary material.
23. Birney D.M., Wagenseller E. J. Am. Chem. Soc. 116:1994;6262.
24. Birney D.M., Xu X., Ham S. Angew. Chem. Int. Ed. 38:1999;189.
25. Quideau S., Looney M.A., Pouységu L., Ham S., Birney D.M. Tetrahedron Lett. 40:1999;615.
26. Schollkopf U., Nozulak J., Groth U. Tetrahedron. 40:1984;1409.
27. March J. Advanced Organic Chemistry. Fourth ed. 1992;Wiley, New York.
28. Foresman J.B., Frisch A.E. Exploring Chemistry with Electronic Structure Methods. Second ed. 1996;Gaussian Inc, Pittsburgh, PA.