Kuanoniamines A, B, C, and D: Pentacyclic Alkaloids from a Tunicate and Its Prosobranch Mollusk Predator Chelynotus semperi

Journal of Organic Chemistry

Volumn 55, Issue 14, 1990, Pages 4426-4431

  Carroll, Anthony R ^a   Scheuer, Paul J ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 8344237053     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00301a040     Document Type: Article

References (29)

1. Karuso, P. In Bioorganic Marine Chemistry; Scheuer, P. J., Ed.; Springer-Verlag; New York 1987; Vol. 1, pp 31–60.
2. Behrens, D. W. Veliger 1980, 22, 323.
3. Lambert, G. Veliger 1980. 22. 340.
4. Lindquist, N.; Fenical, W.; Van Duyne, G.; Clardy, J. J. Org. Chem. 1988, 53, 4570–4574.
5. Andersen, R. J.; Faulkner, D. J.; Cun-heng, H.; Van Duyne, G.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492–5495.
6. Carroll, A. R.; Cooray, N. M.; Poiner, A.; Scheuer, P. J. J. Org. Chem. 1989, 54, 4231–4232.
7. The name kuanoniamine is derived from the Hawaiian word kua-noni meaning change when pertaining to color. This name seems appropriate since the colors of these compounds are extremely sensitive to changes in pH; in neutral and basic solution they are yellow, while in acidic solution they change to brilliant purple.
8. The mollusk was identified as Chelynotus semperi (Bergh) by Dr. Anthony Poiner.
9. The tunicate remains unidentified, but we are endeavoring to obtain a specimen of suitable quality to make identification feasible.
10. Doddrell, D. M.; Pegg, O. T.; Bendall, M. R. J. Magn. Reson. 1982, 48. 323–327.
11. Assignments for all protonated carbons were provided by a 1H-detected heteronuclear one bond 1H-13H correlation experiment (HMQC). 19
12. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093–2094.
13. Bax, A.; Azolos, A.; Dinya, Z.; Sudo, K. J. Am. Chem. Soc. 1986, 108, 8056–8063.
14. Bloor, S. J.; Schmitz, F. J. J. Am. Chem. Soc. 1987, 109, 6134–6137.
15. de Guzman, F. S.; Schmitz, F. J. Tetrahedron Lett. 1989, 30, 1069–1070.
16. Kobayashi, J.; Cheng, J.; Nakamura, H.; Ohizumi, Y. Tetrahedron Lett. 1988, 29, 1177–1180.
17. Gunawardana, G. P.; Kohmoto, S.; Burres, N. S. Tetrahedron Lett. 1989, 30, 4359–4362.
18. Faure, H.; Galy, J.-P.; Elguero, J.; Vincent, E. Can. J. Chem. 1978, 56, 46–55.
19. These l3C NMR assignments were based on information provided by broad-band decoupled and DEPT sequence experiments.
20. Klenar, V. S.; Bax, A. J. Magn. Reson. 1987, 71, 379–383.
21. Schmitz, F. J.; Agarwal, S. K.; Gunasekera, S. P.; Schmidt, P. G.; Shoolery, J. N. J. Am. Chem. Soc. 1983, 105, 4835–4836.
22. Molinski, T. F.; Fahy, E.; Faulkner, D. J.; Van Duyne, G. D.; Clardy, J. J. Org. Chem. 1988, 53, 1340–1341.
23. Gunawardana, G. P.; Kohmoto, S.; Gu-nasekera, S. P.; McConnell, O. J.; Koehn, F. E. J. Am. Chem. Soc. 1988, 110, 4856–4858.
24. Kobayashi, J.; Cheng, J.; Walchli, M. R.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Ohizumi, Y. J. Org. Chem. 1988, 53, 1800–1803.
25. Rudi, A.; Benayashu, Y.; Goldberg, I.; Kashman, Y. Tetrahedron Lett. 1988, 29, 3861–3862.
26. Molinski, T. F.; Ireland, C. M. J. Org. Chem. 1989, 54, 4256–4259.
27. Charyulu, G. A.; McKee, T. C.; Ireland, C. M. Tetrahedron Lett. 1989, 30, 4201–4202.
28. The observation of 4J CHcorrelations, although unusual, is in accordance with the magnitude of 4J CHcouplings reported for pyridine systems (4jc3-h6 = -1.7 Hz, 4jc2-h5 =-0.9 Hz) and benzene systems (4jch = 1.3 Hz)20and is indicative of the greater sensitivity of the HMBC experiment over its detected counterpart, the COLOC experiment. Both HMBC experiments were optimized for detecting 5-Hz coupling.
29. Kalinowski, H. O.; Berger, S.; Braun, S. l3C NMR Spektroskopie; Thieme: Stuttgart, 1984.