Regioselective alkylation of substituted quinones by trialkylboranes

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4473-4476

  Bieber, Lothar W ^a   Rolim Neto, Pedro J ^a   Generino, Regina M ^a  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

1,4 Addition; 1,4 quinones; Radical mechanism; Trialkylboranes

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; 1,4 NAPHTHOQUINONE DERIVATIVE; ALKYL GROUP; BORANE DERIVATIVE; BUTANE; CARBONYL DERIVATIVE; HEXANE; LAWSONE; PENTANE; RADICAL; RESORCINOL; TETRAHYDROFURAN;

ALKYLATION; ANTIBIOTIC BIOSYNTHESIS; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; COPRINUS; DRUG ISOLATION; DRUG SYNTHESIS; HYDROLYSIS; ISOMER; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033546375     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00804-7     Document Type: Article

References (24)

1. 1. Brown, H.C.; Midland, M.M. Angew. Chem. Int. Ed. Engl. 1972, 11, 692.
2. 2. a) Langlais, M.; Buzas, A.; Fréon, P. Compt. Rend. Acad. Sci. Fr. 1961, 253, 2364.
3. b) Gocmen, M.; Soussan, G.; Fréon, P. Bull. Soc. Chim. Fr. 1973, 562.
4. c) Alberola, A.; Gonzalez, A.M.; Ualarduya, J.A.M. An. Quím. 1977, 73, 127.
5. 3. Hawthorne, M.F.; Reintjes, M. J. Am. Chem. Soc. 1965, 87, 4585.
6. 4. Maruyama, K.; Saimoto, K.; Yamamoto, Y. J. Org. Chem. 1978, 43, 4895.
7. 3-oxidation.
8. 6. Anchel, M.; Henvey, A.; Kavanagh, F.; Polatwich, J.; Robbins, W.J. Proc. Nat. Acad. Sci. U.S. 1948, 34, 498.
9. 7. Schildknecht, H.; Bayer, I.; Schmidt, H. Zeitschr. f. Naturf. B 1967, 22, 287.
10. 8. Melo, A.M.; Jardim, M.L.; Santana, C.F.; Lima, O.G.; D'Albuquerque, I.L. Revista do Instituto de Antibióticos, Recife 1974, 14, 9.
11. 9. a) Hjorth, N.; Fregert, S.; Schildknecht, H. Acta Dermat. Venereol. 1969, 49, 552.
12. b) Schildknecht, H. Angew. Chem. Int. Ed. Engl. 1981, 20, 164.
13. 10. R.M.O.C.; Bieber, L.W.; Nascimento, S.C. Acta Amazônica, in press.
14. 11. Zweifel, G.; Brown, H.C. Org. React. 1963, 13, 1.
15. 12. a) Ashley, J.N. J. Chem. Soc. 1937, 1471.
16. b) Höfle, G. Tetrahedron 1976, 32, 1431.
17. c) Wender, P.A.; Rawlins, D.B. Tetrahedron 1992, 48, 7033.
18. d) Zhu, W.; Ford, W.T. J. Mol. Catal. 1993, 78, 367.
19. 13. Fieser, L.F.; Berliner, E.; Bondhus, F.J.; Chang, F.C.; Dauben, W.G.; Ettlinger, M.G.; Fawaz, G.; Fields, M.; Heidelberger, C.; Heymann, H.; Vaughan, W.R.; Wilson, A.G.; Wilson, E.; Moore, E.E.; Moore, M.B.; Zaugg, H.E. J. Am. Chem. Soc. 1948, 70, 3174.
20. 14. a) Khambay, B.P.S.; Batty, D. PCT Int. Appl. WO 96 21,354; Chem. Abstr. 1996, 125, P 195991d.
21. b) Munday, R.; Smith, B.L.; Munday, C.M. Chem. Biol. Interact. 1995, 98, 185.
22. c) Campos-Takaki, G.M.; Steiman, R.; Seigle-Murandi, F.; Silva, A.A.; Bieber, L. Revista Microbiológica 1992, 23, 106.
23. 15. Kabalka, G.W. J. Organomet. Chem. 1971, 33, C25.
24. 16. Jacobsen, N.; Torssell, K. Acta Chem. Scand. 1973, 27, 3211.