Stereospecific Construction of Multiple Contiguous Quaternary Carbons. Total Synthesis of (±)-cis, anti, cis-1,8,12,12-Tetramethyl-4-oxatricyclo[6.4.0.02,6]dodecan-3-ol, a Thapsane Isolated from Thapsia villosa var minor

Journal of Organic Chemistry

Volumn 58, Issue 27, 1993, Pages 7751-7755

  Srikrishna, A ^a   Krishnan, K ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

SESQUITERPENE; THAPSANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0027716569     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00079a020     Document Type: Article

References (43)

1. Lemmich, E.; Jensen, B.; Rasmussen, U. Phytochemistry 1984, 23, 809.
2. Pascual Teresa, J. D.; Moran, J. R.; Grande, M. Chem. Lett. 1985, 865.
3. Pascual Teresa, J. D.; Moran, J. R.; Fernandez, A.; Grande, M. Phytochemistry 1986, 25, 703 and 1171.
4. Smitt, U. W.; Comett, C.; Norup, E.; Christensen, S. B. Phytochemistry 1990, 29, 873.
5. Srikrishna, A.; Krishnan, K. Tetrahedron Lett. 1989, 30, 6577.
6. Srikrishna, A.; Sundarababu, G. Tetrahedron 1990, 46, 3601.
7. Srikrishna, A.; Krishnan, K. Indian J. Chem. 1990, 29B, 879.
8. Srikrishna, A.; Sundarababu, G. Tetrahedron 1991, 47, 481.
9. Srikrishna, A.; Nagaraju, S. J. Chem. Soc., Perkin Trans. 1 1991, 657.
10. Srikrishna, A.; Krishnan, K. Tetrahedron 1992, 48, 3429.
11. Srikrishna, A.; Krishnan, K. J. Chem. Soc., Perkin Trans. 1 1993, 667.
12. Preliminary communication; Srikrishna, A.; Krishnan, K. J. Chem. Soc., Chem. Commun. 1991, 1693.
13. Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
14. McKenzie, T. C. Org. Prep. Proc. Int. 1987, 435.
15. Stork, G.; Ficini, J. J. Am. Chem. Soc. 1961, 83, 4678.
16. Burke, S. D.; Grieco, P. A. Org. React. 1979, 26, 361.
17. Padwa, A.; Krumps, K. E. Tetrahedron 1992, 48, 5385.
18. Jalali-Naini, M.; Guillerm, D.; Lallemand, J. Y. Tetrahedron 1983, 39, 749.
19. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258.
20. Mc Murry, J. E.; Blaszczak, L. C. J. Org. Chem. 1974, 39, 2217;
21. Büchi, G.; White, J. D. J. Am. Chem. Soc. 1964, 86, 2884.
22. Lee, E.; Shin, I.-J.; Kim, T.-S. J. Am. Chem. Soc. 1990, 112, 260.
23. Norin, T. Acta Chem. Scand. 1963, 17, 738.
24. Norin, T. Acta Chem. Scand. 1965, 19, 1289.
25. Dauben, W. G.; Deviny, E. J. J. Org. Chem., 1966, 31, 3794.
26. Dauben, W. G.; Wolf, R. E. J. Org. Chem. 1970, 35, 374 and 2361.
27. Srikrishna, A.; Krishnan, K.; Yelamaggad, C. V. Tetrahedron 1992, 48, 9725.
28. Mirrington, R. N.; Schmalzl, K. J. J. Org. Chem. 1972, 37, 2871.
29. Stork, G.; Darling, S. D. J. Am. Chem. Soc. 1960, 82, 1912.
30. Stork, G.; Darling, S. D. J. Am. Chem. Soc. 1964, 86, 1761.
31. Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945.
32. Janaki, S.; Subba Rao, G. S. R. Indian J. Chem. 1988, 27B, 505.
33. Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1983, 24, 5325.
34. Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G.; Ranu, B. C.; Papadopolous. Tetrahedron 1987, 43, 5685.
35. Newcomb, M.; Glenn, A. G.; Williams, W. G. J. Org. Chem. 1989, 54, 2675.
36. Freeman, J. P. Chem. Ind. (London) 1959, 1254.
37. Helquist, P. Methylene and nonfunctionalized alkylidene transfer to form cyclopropanes. In Comprehensive organic synthesis. Selectivity, strategy and efficiency in modern organic chemistry; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol 4, p 387 and refs cited therein.
38. See also Krief, A.; Dubois, P. Tetrahedron Lett. 1993, 34, 2691.
39. Loim, L. M.; Parnes, Z. N.; Vasil'eva, S. P.; Kursanov, D. N. J. Org. Chem. USSR 1972, 8, 902.
40. Kraus, G. A.; Frazier, K. A.; Roth, B. D.; Taschner, M. J.; Neuenschwander, K. J. Org. Chem. 1981, 46, 2417.
41. Regitz, M.; Hocker, J.; Liedhegener, A. Organic Syntheses Wiley: New York, 1973; Collect. Vol. V, pp 179.
42. Womack, E. B.; Nelson, A. B. Organic Syntheses Wiley: New York, 1973; Collect. Vol. V, pp 392.
43. Rempel, G. A.; Legzdins, P.; Smith, H.; Wilkinson, G. Inorganic Synthesis; McGraw-Hill, Inc.: New York, 1972; Vol. 13, p 90.