An expeditious route to CoQ(n), Vitamins K1 and K2, and related allylated para-quinones utilizing Ni(0) catalysis

Tetrahedron

Volumn 54, Issue 7, 1998, Pages 1241-1253

  Lipshutz, Bruce H ^a   Kim, Sung Kyu ^a   Mollard, Paul ^a   Stevens, Kirk L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FARNOQUINONE; PHYTOMENADIONE; QUINONE DERIVATIVE; UBIQUINONE;

ARTICLE; CATALYSIS; PRIORITY JOURNAL;

EID: 0032510216     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10222-8     Document Type: Article

References (21)

1. 1. (a) Thomson, R.H. Naturally Occurring Quinones, 3rd ed., Academic Press, New York, 1987;
2. (b) The Chemistry of the Quinonoid Compounds; Rappoport, Z. Ed.; Wiley: New York, 1988;
3. (c) The Chemistry of Quinonoid Compounds; Patai, S. Ed. Interscience: New York, 1974.
4. 2. Lipshutz, B. H.; Bülow, G.; Lowe, R. F.; Stevens, K. L., J. Am. Chem. Soc. 1996, 118, 5512.
5. 3. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252; Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639; Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31; Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
6. 3. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252; Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639; Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31; Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
7. 3. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252; Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639; Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31; Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
8. 3. Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252; Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639; Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31; Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
9. 4. Keinan, E.; Eren, D J. Org. Chem., 1987, 52, 3872; Shiraishi, M.; Terao, S. J. Chem. Soc., Perkin Trans. 1, 1983, 1951.
10. 4. Keinan, E.; Eren, D J. Org. Chem., 1987, 52, 3872; Shiraishi, M.; Terao, S. J. Chem. Soc., Perkin Trans. 1, 1983, 1951.
11. 9 is $414.95 / 10 mg (or $41,495 per gram).
12. 6. The bromomethylated analogue has been used previously in couplings with a vinylcopper derivative; see: Rüttimann, A. Chimia, 1986, 40, 290.
13. 7 Lipshutz, B.H.; Bulow, G.; Stevens, K.L.; Lowe, R. Tetrahedron, 1996, 52, 7265.
14. 2 see Tso, H-H.; Chen, Y-J. J. Chem. Research 1995, 104; Kozhevnikov, I. V.; Kilikov, S. M.; Chukaeva, N. G.; Kirsanov, A. T.; Letunova, A. B.; Blinova, V. I. React. Kinet. Catal. Lett., 1992, 47, 59; Schmid, R.; Antoulas, S.; Rüttimann, A.; Schmid, M.; Vecchi, M.; Weiser, H. Helv. Chem. Acta., 1990, 73, 1276.
15. 2 see Tso, H-H.; Chen, Y-J. J. Chem. Research 1995, 104; Kozhevnikov, I. V.; Kilikov, S. M.; Chukaeva, N. G.; Kirsanov, A. T.; Letunova, A. B.; Blinova, V. I. React. Kinet. Catal. Lett., 1992, 47, 59; Schmid, R.; Antoulas, S.; Rüttimann, A.; Schmid, M.; Vecchi, M.; Weiser, H. Helv. Chem. Acta., 1990, 73, 1276.
16. 2 see Tso, H-H.; Chen, Y-J. J. Chem. Research 1995, 104; Kozhevnikov, I. V.; Kilikov, S. M.; Chukaeva, N. G.; Kirsanov, A. T.; Letunova, A. B.; Blinova, V. I. React. Kinet. Catal. Lett., 1992, 47, 59; Schmid, R.; Antoulas, S.; Rüttimann, A.; Schmid, M.; Vecchi, M.; Weiser, H. Helv. Chem. Acta., 1990, 73, 1276.
17. n, see a) Terao, S.; Kato, K.; Shiraishi, M.; Morimoto, H. J. Chem. Soc., Perkin Trans. I 1978, 1101;
18. b) Naruta, Y. J. Org. Chem. 1980, 45, 4097;
19. c) Eren, D.; Keinan, E. J. Am. Chem. Soc. 1988, 110, 4356 and references cited therein;
20. d) Rüttimann, A.; Lorenz, P. Helvetica Chimica Acta 1990, 73, 790;
21. e) Van Lient, W.B.S.; Steggerda, W.F.; Esmeijer, R.; Lugtenburg, J. Recueil des Travaux Chimiques des Pays-Bays 1994, 113, 153;