Intramolecular Diels-Alder reaction in 1-oxaspiro[2.5]octa-5,7-dien-4- one and sigmatropic shifts in excited states: Novel route to sterpuranes and linear triquinanes: Formal total synthesis of (±)-coriolin

Chemical Communications

Volumn , Issue 24, 1999, Pages 2519-2520

  Singh, Vishwakarma ^a   Alam, S Q ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

SESQUITERPENE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033592856     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908223i     Document Type: Article

References (40)

1. Isolation of 1-3: (a) W. A. Ayer and M. H. Saeedi-Ghomi, Can. J. Chem., 1981, 59, 2536;
2. (b) O. Sterner, T. Anke, W. S. Sheldrick and W. Steglich, Tetrahedron, 1990, 46, 2389;
3. (c) J.-L. Xie, L.-P. Li and Z.-Q. Dai, J. Org. Chem., 1992, 57, 2313.
4. Isolation of other sterpuranes: (d) C. Abell and A. P. Leech, Tetrahedron Lett., 1987, 28, 4887;
5. (e) G. Cimino, A. D. Giulio, S. D. Rosa and S. D. Stefano, Tetrahedron, 1989, 45, 6479;
6. (f) W. A. Ayer and L. M. Browne, Tetrahedron, 1981, 37, 2199.
7. T. Takeuchi, H. Iinuma, J. Iwanaga, S. Takahashi, T. Takita and H. Umezawa, J. Antibiot., 1969, 22, 215; S. Takahashi, H. Naganawa, H. Iinuma, T. Takita, K. Maeda and H. Umezawa, Tetrahedron Lett., 1971, 1955.
8. T. Takeuchi, H. Iinuma, J. Iwanaga, S. Takahashi, T. Takita and H. Umezawa, J. Antibiot., 1969, 22, 215; S. Takahashi, H. Naganawa, H. Iinuma, T. Takita, K. Maeda and H. Umezawa, Tetrahedron Lett., 1971, 1955.
9. K. Domon, K. Masuya, K. Tanino and I. Kuwajima, Tetrahedron Lett., 1997, 38, 465; V. Singh and B. Samanta, Tetrahedron Lett., 1999, 40, 383; H. Mizuno, K. Domon, K. Masuya, K. Tanino and I. Kuwajima, J. Org. Chem., 1999, 64, 2648. For other references on synthesis of coriolin see ref. 4(a).
10. K. Domon, K. Masuya, K. Tanino and I. Kuwajima, Tetrahedron Lett., 1997, 38, 465; V. Singh and B. Samanta, Tetrahedron Lett., 1999, 40, 383; H. Mizuno, K. Domon, K. Masuya, K. Tanino and I. Kuwajima, J. Org. Chem., 1999, 64, 2648. For other references on synthesis of coriolin see ref. 4(a).
11. K. Domon, K. Masuya, K. Tanino and I. Kuwajima, Tetrahedron Lett., 1997, 38, 465; V. Singh and B. Samanta, Tetrahedron Lett., 1999, 40, 383; H. Mizuno, K. Domon, K. Masuya, K. Tanino and I. Kuwajima, J. Org. Chem., 1999, 64, 2648. For other references on synthesis of coriolin see ref. 4(a).
12. (a) For excellent review on polyquinane natural products: G. Mehta and A. Srikrishna, Chem. Rev., 1997, 97, 671 and references cited therein;
13. (b) R. D. Little, Chem. Rev., 1996, 96, 93;
14. (c) V. Singh and B. Thomas, Tetrahedron, 1998, 54, 3647;
15. (c) L. A. Paquette, Top. Curr. Chem., 1984, 119, 1.
16. K. Masuya, K. Domon, K. Tanino and I. Kuwajima, J. Am. Chem. Soc., 1998, 120, 1724; M. Lautens and J. Blackwell, Synthesis, 1998, 537; V. Krishnamurthy and V. H. Rawal, J. Braz. Chem. Soc., 1998, 9, 341.
17. K. Masuya, K. Domon, K. Tanino and I. Kuwajima, J. Am. Chem. Soc., 1998, 120, 1724; M. Lautens and J. Blackwell, Synthesis, 1998, 537; V. Krishnamurthy and V. H. Rawal, J. Braz. Chem. Soc., 1998, 9, 341.
18. K. Masuya, K. Domon, K. Tanino and I. Kuwajima, J. Am. Chem. Soc., 1998, 120, 1724; M. Lautens and J. Blackwell, Synthesis, 1998, 537; V. Krishnamurthy and V. H. Rawal, J. Braz. Chem. Soc., 1998, 9, 341.
19. (a) Y. Murata, T. Ohtsuka, H. Shirahama and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4313;
20. (b) L. Moens, M. M. Baizer and R. D. Little, J. Org. Chem., 1986, 51, 4497;
21. (c) L. A. Paquette, H.-S. Lin, B. P. Gunn and M. J. Coghlan, J. Am. Chem. Soc., 1988, 110, 5818;
22. (d) S.-K. Zhao and P. Helquist, J. Org. Chem., 1990, 55, 5820;
23. (e) G. M. Strunz, R. Bethell, M. T. Dumas and N. Boyonoski, Can. J. Chem., 1997, 75, 742;
24. (f) O. J. Birkenes, T. V. Hansen, S. M'dachi, L. Skattebol and Y. Stenstrom, Acta. Chem. Scand., 1998, 52, 806;
25. (g) R. A. Gibbs, K. Bartels, R. W. K. Lee and W. H. Okamura, J. Am. Chem. Soc., 1989, 111, 3717;
26. (h) N. Krause, Liebigs Ann. Chem., 1993, 521;
27. (i) A. Arnone, C. D. Gregorio, G. Nasini and O. V. D. Pava, J. Chem. Soc., Perkin Trans. 1, 1997, 1523.
28. V. Singh, Acc. Chem. Res., 1999, 32, 324.
29. D. I. Schuster, in Rearrangement in Ground and Excited States, ed. P. deMayo, Academic Press, New York, 1980, vol. 3; V. Singh and M. Porinchu, Tetrahedron, 1996, 52, 7087.
30. D. I. Schuster, in Rearrangement in Ground and Excited States, ed. P. deMayo, Academic Press, New York, 1980, vol. 3; V. Singh and M. Porinchu, Tetrahedron, 1996, 52, 7087.
31. H. E. Zimmerman and D. Armesto, Chem. Rev., 1996, 96, 3065.
32. K. Tsubaki, T. Otsubo, K. Tanaka, K. Fuji and T. Kinoshita, J. Org. Chem., 1998, 63, 3260.
33. E. Adler and K. Holmberg, Acta. Chem. Scand., 1974, 28B, 465; V. Singh, A. V. Bedekar and M. R. Caira, J. Chem. Res. (S), 1995, 452.
34. E. Adler and K. Holmberg, Acta. Chem. Scand., 1974, 28B, 465; V. Singh, A. V. Bedekar and M. R. Caira, J. Chem. Res. (S), 1995, 452.
35. M. Demuth and W. Hinsken, Angew. Chem., Int. Ed. Engl., 1985, 24, 973; J.-T Hwang and C.-C. Liao, Tetrahedron. Lett., 1991, 32, 6583.
36. M. Demuth and W. Hinsken, Angew. Chem., Int. Ed. Engl., 1985, 24, 973; J.-T Hwang and C.-C. Liao, Tetrahedron. Lett., 1991, 32, 6583.
37. For synthesis of tetracyclic systems of type 16 by metu-photocycloaddition, P. A. Wender and J. J. Howbert, Tetrahedron Lett., 1982, 23, 3983.
38. E. J. Enholm and Z.J. Jia, J. Org. Chem., 1997, 62, 174.
39. R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen and L. H. M. Horcher, Tetrahedron, 1985, 41, 3479; L. V. Hijfte, R. D. Little, J. L. Petersen and K. D. Moeller, J. Org. Chem., 1987, 52, 4647.
40. R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen and L. H. M. Horcher, Tetrahedron, 1985, 41, 3479; L. V. Hijfte, R. D. Little, J. L. Petersen and K. D. Moeller, J. Org. Chem., 1987, 52, 4647.