Saludimerines A and B, novel-type dimeric alkaloids with stereogenic centers and configurationally semistable biaryl axes

Journal of Organic Chemistry

Volumn 69, Issue 25, 2004, Pages 8602-8608

  Bracher, Franz ^a   Eisenreich, Wolfram J ^a   Mühlbacher, Jörg ^b,c   Dreyer, Michael ^b   Bringmann, Gerhard ^b  

^a UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; FORESTRY; METHANOL; MONOMERS; OXIDATION; PROTONS; SYNTHESIS (CHEMICAL);

BIOMIMETIC OXIDATIVE COUPLING; CIRCULAR DICHROSIM (CD); SALUDIMERINES; SPECTROSCOPIC METHODS;

AMINES;

ALKALOID; SALUDIMERINE A; SALUDIMERINE B; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CROTON; DIMERIZATION; DRUG ISOLATION; ENANTIOMER; MOLECULAR INTERACTION; PHYTOCHEMISTRY; QUANTUM CHEMISTRY; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MORPHINE DERIVATIVES; PLANT LEAVES; PLANTS, MEDICINAL; STEREOISOMERISM;

ALKALOIDS; CROTON; DIMERS; EUPHORBIA; MONOMERS; OXIDATION; PROTONS; QUANTUM CHEMISTRY; TREES;

EID: 10044254631     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048631p     Document Type: Article

References (35)

1. Weber, J.; Hecker, E. Experientia 1978, 34, 679-682.
2. Farnsworth, N. R.; Blomster, R. N.; Messmer, W. M.; King, J. C.; Persinos, G. J.; Wilkes, D. J. Lloydia 1969, 32, 1-28.
3. Stuart, K.; Chambers, C.; Byfield, D. J. Chem. Soc. C 1969, 1681-1684.
4. Charris, J.; Dominguez, J.; de la Rosa, C.; Caro, C. Biochem. Syst. Ecol. 2000, 28, 795-797.
5. Eisenreich, W. J.; Höfner, G.; Bracher, F. Nat. Prod. Res. 2003, 17, 437-440.
6. Eisenreich, W. J.; Bracher F. Nat. Prod. Lett. 2001, 15, 147-150.
7. Amaral, A.; Barnes, R. Phytochemistry 1998, 47, 1445-1447.
8. Barnes, R. A.; Soeiro, O. M. Phytochemistry 1981, 20, 543-544.
9. Strictly speaking, these compounds should rather be addressed as "dehydrodimers"; still, for reasons of simplicity, the term "dimer" (like also "monomer" for the precursor) will be used throughout this paper.
10. Chambers, C.; Haynes, L. J.; Stuart, K. L. J. Chem. Soc., Chem. Commun. 1966, 449.
11. Minawikawa, J.-I.; Iijima, I.; Brossi, A. Heterocycles 1978, 10, 79-84.
12. Bentley, K. W.; Dyke, S. F. J. Chem. Soc. 1959, 2574-2577.
13. Bringmann, G.; Günther, C.; Ochse, M.; Schupp, O.; Tasler, S. Prog. Chem. Org. Nat. Prod. (Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Tamm, C., Eds.) Wien 2001, 82, 1-249.
14. Govindachari, T. R.; Nagarayan, K.; Parthasarathy, P. C.; Rajagopalan, T. G.; Desai, H. K.; Chen, S. L.; Nakanishi, K. J. Chem. Soc., Perkin Trans. 1 1974, 12, 1413-1417.
15. Bringmann, G.; Teltschik, F.; Michel, M.; Busemann, S.; Rückert, M.; Haller, R.; Bär, S.; Robertson, A.; Kaminsky, R. Phytochemistry 1999, 52, 321-332.
16. Bringmann, G.; Dreyer, M.; Faber, J.; Dalsgaard, P. W.; Staerk, D.; Jaroszewski, J.; Ndangalasi, H.; Mbago, F.; Brun, R.; Reichert, M.; Maksimenka, K.; Brogger-Christensen, S. J. Nat. Prod. 2003, 66, 1159-1165.
17. Nakanishi, K.; Berova, N.; Woody, R. W. In The Exciton Chirality Method in Circular Dichroism, Principles and Applications; Oxford University Press: Oxford, 1994.
18. Bringmann, G.; Busemann, S. In Natural Product Analysis; Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden, 1998; pp 195-212.
19. Bringmann, G.; Mühlbacher, J.; Messer, K.; Dreyer, M.; Ebel, R.; Nugroho, B. W.; Wray, V.; Proksch, P. J. Nat. Prod. 2003, 66, 80-85.
20. Meyring, M.; Mühlbacher, J.; Messer, K.; Kastner-Pustet, N.; Bringmann, G.; Mannschreck, A.; Blaschke, G. Anal. Chem. 2002, 74, 3726-3735.
21. Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfarth, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703-2711.
22. Bringmann, G.; Kraus, J.; Menche, D.; Messer, K. Tetrahedron 1999, 55, 7563-7572.
23. Bringmann, G.; Pabst, T.; Henschel, P.; Kraus, J.; Peters, K.; Peters, E.-M.; Rycroft, D. S.; Connolly, J. J. Am. Chem. Soc. 2000, 122, 9127-9133.
24. Bringmann, G.; Mühlbacher, J.; Reichert, M.; Dreyer, M.; Kolz, J.; Speicher, A. J. Am. Chem. Soc. 2004, 126, 9283-9290.
25. SYBYL: Tripos Associates, 1699 Hanley Road, Suite 303, St. Louis, MO, 63144.
26. Bringmann, G.; Gulden, K.-P.; Hallock, Y. F.; Manfredi, K. P.; Cardellina, J. H., II; Boyd, M. R.; Kramer, B.; Fleischhauer, J. Tetrahedron 1994, 50, 7807-7814.
27. Bringmann, G.; Zagst, R.; Reuscher, H.; Aké Assi, L. Phytochemistry 1992, 31, 4011-4014.
28. Hallock, Y. F.; Manfredi, K. P.; Blunt, J. W.; Cardellina, J. H., II; Schäffer, M.; Gulden, K.-P.; Bringmann, G.; Lee, A. Y.; Clardy, J.; François, G.; Boyd, M. R. J. Org. Chem. 1994, 59, 6349-6355.
29. Bringmann, G.; Koppler, D.; Scheutzow, D.; Porzel, A. Magn. Reson. Chem. 1997, 35, 297-301.
30. Bringmann, G.; Saeb, W.; Koppler, D.; François G. Tetrahedron 1996, 52, 13409-13418.
31. Sariyar, G.; Freyer, A. J.; Guinaudeau, H.; Shamma, M. J. Nat. Prod. 1990, 53, 1383-1386.
32. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690.
33. Downing, J. W. Program package BDZDO/MCDSPD, Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO; modified by Fleischhauer, J.; Schleker, W.; Kramer, B.; ported to Linux by Gulden, K.-P.
34. Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807-1813.
35. Gaussian 98 (Revision A.7). 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.