A scalemic synthesis of the scopadulcic acid skeleton. I: An efficient γ-alkylation at C-9 in abietane framework and subsequent aldol reaction

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8459-8462

  Tagat, Jayaram R ^b   McCombie, Stuart W ^a   Puar, Mohindar S ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 16144365888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01947-8     Document Type: Article

References (14)

1. 1. Hayashi, T.; Kishi, M.; Kawasaki, M.; Arisawa, M.; Shimizu, M.; Suzuki, S.; Yoshizaki, M.; Morita, N.; Tezuka, Y.; Kikuchi, T.; Berganza, L. H.; Ferro, E.; Basualdo, I. Tetrahedron Lett. 1987, 28, 3693.
2. 2. a) Hayashi, K.; Niwayama, S.; Hayashi, T.; Nago, R.; Ochiai, H.; Morita, N. Antiviral Research 1988, 9, 345.
3. b) Miyahara, T.; Hayashi, T.; Matsuda, S.; Yamada, R.; Ikeda, K.; Tonoyama, H.; Komiyama, H.; Matsumoto, M.; Nemoto, N.; Sankawa, U. Bioorg. Med. Chem. Lett. 1996, 6, 1037.
4. 3. a) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042.
5. b) Ziegler, F. E.; Wallace, O. B. J. Org. Chem. 1995, 60, 3626.
6. c) Robichaud, A.; Meyers, A. I. J. Org. Chem. 1991, 56, 2607.
7. d) Fox, M. E.; Li, C.; O'Conner, S. J.; Overman, L. E. Abstracts of Papers, 210th National Meeting of the American Chemical Society, Chicago, II, August 20-24, 1995. ORGN 285.
8. 4. Tagat, J. R.; Nazareno, D. V.; Puar, M. S.; McCombie, S. W.; Ganguly, A. K. Bioorg. Med. Chem. Lett. 1994, 4, 1101.
9. 5. Abad, A.; Arno, M.; Domingo, L. R.; Zaragosa, R. J. Tetrahedron 1985,41, 4937
10. 6. Kirk, D. N.; Wiles, J. M. J. C. S. Chem. Commun. 1970, 1015.
11. 7. Tagat, J. R.; McCombie, S. W.; Ganguly, A. K.; Puar, M. S. Abstracts of Papers, 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992. ORGN 307.
12. 8. Fleming, I.; Goldhill, J.; Paterson, I. Tetrahedron Lett. 1979, 3209.
13. 9. Kraus, G. A.; Thomas, P. J.; Bougie, D.; Chen, L. J. Org. Chem. 1990, 55, 1624 : The corresponding 3,3-diphenyl-2-propenyl halides were not as effective as the carbinol 10.
14. 3): δ 0.74 (s, 3H-minor), 0.92 (s, 3H-major), 1.0 (m,1H), 1.1(s,3H-major), 1.14 (s,3H-minor), 1.2 (s,3H-major), 1.23 (s,3H-minor), 1.25-1.35 (m, 3H), 1.4-1.75 (m,6H), 1.8 (d, J = 11.6Hz, 1H), 1.95 (dd, J=4,13 Hz, 1H), 2.07 (dd, J=2.8,12.8 Hz, 1H), 2.17 (dd, J=2,7 Hz,1H), 2.22 (dd, J =2,7 Hz, 1H), 2.48 (m, 2H), 3.62 (s, 3H-major), 3.65 (s, 3H-minor), 3.85 (t, J=2.5Hz,1H-major), 4.2 (m, 1H-minor), 5.6 (s, 1H-major) and 5.8 (s, 1H-minor).