The first synthesis of a 2-epi-cedrene isoprenologue by means of an electrochemical method in the key step

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4043-4046

  Takakura, Hiroyuki ^a   Toyoda, Kunihiro ^a   Yamamura, Shosuke ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOPRENE; PHENOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029972958     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00757-5     Document Type: Article

References (20)

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9. (b) Forster, P. G.; Ghisalberti, E. I.; Jefferies, P. R. J. Nat. Prod. 1993, 56, 147-152.
10. 3) δ 1.73 (3H, s), 1.74-2.00 (4H, complex), 2.04 (3H, s), 2.83 (1H, m), 3.68 (1H, dd, J = 8.6, 5.6 Hz), 3.78 (1H, dd, J = 8.6, 5.6 Hz), 3.80 (3H, s), 3.82 (3H, s), 4.47 (2H, s), 4.53 (1H, d, J = 11.9 Hz), 4.61 (1H, d, J = 11.9 Hz), 5.34 (1H, t, J = 7.3 Hz), 6.51 (2H, s), 7.27-7.34 (5H, complex).
11. The anodic oxidation of 3 was carried out at room temperature under an argon atmosphere using a 200 m1 glassy carbon beaker [GC-20, Tokai Carbon Co. Ltd.] and a platinum wire tip as an anode and a cathode, respectively. On electrolysis under aerobic condition, the total yield of 2 and 4 was very low.
12. 3) δ 1.66 (3H, d, J = 1.0Hz), 5.26 (1H, br.s).
13. 3, THF; ii) KH, BnBr, DMF (50% overall yield) Scheme 3.
14. 6-position.
15. Ando, M.; Wada, K.; Takase, K. Tetrahedron Lett. 1985, 26, 235-238. Ando, M.; Ohara, H.; Takase, K. Chemistry. Lett. 1986, 879-882.
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17. Congreve, M. S.; Davison, E. C.; Fuhry, M. A. M.; Holmes, A. B.; Payne, A. N.; Robinson, R. A.; Ward, S. E. Synlett 1993, 663-664.
18. 3) δ 12.3, 23.1, 24.0, 24.5, 24.6, 29.7, 34.1, 34.9, 42.1, 48.2, 51.1, 51.6, 51.8, 54.4, 60.6, 120.2, 127.3, 140.3, 143.1, 168.7, 180.2.
19. (a) Landry, D. W. Tetrahedron 1983, 39, 2761-2768 and many references cited therein,
20. (b) Stork, G.; Clark, F. H. J. Am. Chem. Soc. 1955, 77, 1072-1073.