A stereoselective total synthesis of (-)-rishitin

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1889-1892

  Chen, Jiong ^a   Marx, John N ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RISHITIN; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 0031575778     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00228-1     Document Type: Article

References (17)

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2. b) T. Masamuni, T.; Murai, A.; Takasuki, M.; Matsunaga, A.; Kastui, N.; Sato, N; Tomiyama, K. Bull. Chem. Soc. Jpn. 1977, 50, 1201.
3. 2) Murai, A.; Nishizakura, K.; Katsui, N.; Masamuni, T. Bull. Chem. Soc. Jpn. 1977, 50, 1206.
4. 3) a) Johnson, W. S.; Pappo, R.; Johns, W. F., J. Amer. Chem. Soc. 1956, 78, 6339.
5. b) Windholz, T. B.; Brown, R. D.; Patchett, A. A. Steroids 1965, 6, 409.
6. c) MacSweeney, D. F.; Ramage, R. Tetrahedron 1971, 27, 1481.
7. d) Cotsaris, E.; Paddon-Row, M. N. J. Chem. Soc., Perkin Trans 2 1984, 1487.
8. 4) a) Stork, G.; Baine, N. H. J. Am. Chem. Soc. 1982, 104, 2321;
9. b) Stork, G.; Baine, N. H. Tetrahedron Lett. 1985, 26, 5927.
10. 5) The work was carried out on the model compound 5 by locating the transition states of the two possible pathways and calculating the energies of them. For the AM1 program, see Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. P. J. Amer. Chem. Soc. 1985, 107, 3902.
11. 6) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 3337.
12. 7) Mori, K.; Fukamatsu, K. Liebigs Ann. Chem. 1992, 489.
13. 8) Rubottom, G. M.; Kim, C.-W., J. Org. Chem. 1983, 48, 1550.
14. 9) Vig, O. P.; Sharma, S. D.; Raj, I. Indian J. Chem. 1966, 4, 127.
15. 10) a) Barton, D. H. R.; O'Brien, R. E.; Stemhell, S. J. Chem. Soc. 1962, 470;
16. b) Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron Lett. 1983, 24, 1605.
17. 3) of selected compounds: 11: 1.44 (s, 3H), 1.48 (s, 3H), 3.23 (dd, J=10.7, 5.1, 1H), 3.35 (dd, J=10.7, 4.6, 1H), 3.64 (m, 1H), 4.17 (dd, J=7.2, 7.1, 1H), 5.31 (ddd, J=10.2, 1.8, 1.4, 1H), 5.42 (ddd, J=16.9, 1.8, 1.4, 1H), 5.87 (ddd, J=16.9, 10.2, 7.2, 1H)). 16: 0.18 (s, 9H), 1.2 - 1.45 (m, 1H), 1.55 - 1.85 (m, 1H), 1.73 (br s, 3H), 1.90 - 2.15 (m, 4H), 2.15 - 2.25 (m, 1H), 4.72 (br s, 2H), 4.8 (br s, 1H). 19: 1.15 - 1.50 (m, 2H), 1.37 (s, 3H), 1.40 (s, 3H), 1.50 - 1.80 (m, 1H), 1.74 (br s, 3H), 1.85 - 2.05 (m, 1H), 2.05 - 2.50 (m, 5H), 2.50 - 2.65 (m, 1H), 3.79 (m, 1H), 3.94 (t, J=7.2, 1H), 4.73 (brs, 1H), 4.76 (br s, 1H), 5.28 (ddd, J=10.2, 1.8, 1.4, 1H), 5.42 (ddd, J=16.9, 1.8, 1.4, 1H), 5.86 (ddd, J=16.9, 10.2, 7.2, 1H). 20: 1.41 (s, 3H), 1.45 (s, 3H), 1.5 - 1.8 (m, 2H), 1.72 (br s, 3H), 2.2 - 2.8 (m, 7H), 3.86 m, 1H), 4.14 (m, 1H), 4.71 (brs, 1H), 4.74 (br s, 1H), 5.28 (dd, J=10-0, 1.6, 1H), 5.43 (dd, J=17.0, 1.6, 1H), 5.85 (ddd, J=17.0, 10.0, 7.0, 1H). CMR data (50 MHz) of selected compounds: 11: 4.7, 27.2, 27.2, 79.1, 82.7, 109.5, 119.4, 134.7. 16: 0.30, 20.7, 23.7, 27.3, 35.1, 41.8, 103.4, 108.7, 149.1, 149.8 19: 20.4, 26.9, 27.3, 30.7, 31.8, 34.2, 47.2, 47.3, 47.4, 79.2, 83.2, 108.6, 109.7, 119.0, 135.0, 147.4, 211.7. 20: 16.4, 21.1, 26.4, 27.2, 27.2, 30.2, 30.9, 35.9, 39.2, 40.2, 76.1, 84.1, 109.0, 109.4, 125.6, 129.7, 148.7.