Synthesis of alkylphenols and alkylcatechols from the marine mollusc Haminoea callidegenita

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3975-3978

  Izzo, Irene ^a   De Caro, Salvatore ^a   De Riccardis, Francesco ^a   Spinella, Aldo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

alkylphenols; Haminoea callidegenita; palladium catalysts; pheromones

Indexed keywords

CATECHOL DERIVATIVE; PHENOL DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CYTOTOXICITY; DNA REPAIR; DRUG STRUCTURE; DRUG SYNTHESIS; MOLLUSC; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034697497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00532-3     Document Type: Article

References (24)

1. Spinella, A.; Alvarez, L. A.; Cimino, G. Tetrahedron Lett. 1998, 39, 2005-2008.
2. Cimino, G.; Passeggio, A.; Sodano, G.; Spinella, A.; Villani, G. Experientia 1991, 47, 61-63.
3. (a) Sleeper, H. L.; Fenical, W. J. Am. Chem. Soc. 1977, 99, 2367-2368.
4. (b) Fenical, W.; Sleeper, H. L.; Paul, V. J.; Stallard, U. O.; Sun, H. H. Pure Appl. Chem. 1979, 51, 1865-1874.
5. (c) Sleeper, H. L.; Paul, V. J.; Fenical, W. J. Chem. Ecol. 1980, 6, 57-70.
6. (a) Wasser, Ch.; Silva, F.; Rodriguez, E. Experientia 1990, 46, 500-502.
7. (b) Singh, U. S.; Scannell, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699
8. (c) Orjala, J.; Mian, P.; Rali, T.; Sticher O. J. Nat. Prod. 1998, 61, 939-941.
9. 13C NMR, EI-MS spectra, and elemental analyses) were obtained for all the new compounds.
10. Aizpurua, J. M.; Palomo, C. Tetrahedron Lett. 1985, 26, 475-476.
11. Iwagami, H.; Nakazawa, M.; Yatagai, M.; Hijiya, T.; Honda, Y.; Naora, H.; Ohnuki, T.; Yukawa, T. Bull. Chem. Soc. Jpn. 1990, 63, 3073-3081.
12. Herscovici, J.; Antonakis, K. J. Chem. Soc., Chem. Commun. 1980, 561-562.
13. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410; Evans, D.A.; Ng, H. P.; Tetrahedron Lett. 1993, 34, 2229-2232.
14. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410; Evans, D.A.; Ng, H. P.; Tetrahedron Lett. 1993, 34, 2229-2232.
15. 1H NMR resonance of their vinylic protons (E isomer: δ 6.01, d, J=14.3 Hz and 6.54, dt, J=14.3, 7.3 Hz; Z isomer: δ 6.21, m, and 7.07, d, J=8.2 Hz).
16. 1H NMR resonance of their vinylic protons (E isomer:δ 6.03, d, J=14.4 Hz and 6.52, m; Z isomer: δ 6.22, m and 6.64, d, J=8.2 Hz).
17. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524 and references therein.
18. Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138-2152.
19. Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854-1862.
20. Aksela, R.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1163-1176.
21. 3, 100 MHz): δ 146.9, 135.4, 131.7, 129.6, 98.8, 66.9, 62.3, 32.9, 30.7, 29.1 (×3), 27.2 (×3), 25.5, 19.6, 13.6 (×3), 9.5 (×3).
22. 13C NMR values with literature data (Wehrli, F. W.; Nishida, T. Progr. Chem. Org. Nat. Products 1979, 36, p. 128).
23. 3, 100 MHz): δ 153.7, 134.4, 133.7, 132.2, 131.3, 131.0, 130.9, 130.2, 129.2 (×2), 119.8 (×2), 98.8, 67.0, 62.3, 35.0, 34.8, 33.2, 30.7, 25.7 (×3), 25.5, 19.6, 18.2, -2.8 (×2).
24. 3, 100 MHz): δ 147.3, 145.5, 134.9, 133.5, 132.2, 131.2, 131.0, 130.8, 130.1, 120.4, 117.4, 108.6, 107.8, 98.7, 66.9, 62.2, 35.5, 34.9, 33.2, 30.6, 25.8 (×2), 25.4, 19.5.