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

Abstract

A novel, stereoselective synthesis of sterpuranes and coriolin via modulation of the photochemical reactivity of a tricyclic system having a β,γ-enone chromophore, which was assembled via intramolecular π^4s + π^2s cycloaddition of 1-oxaspiro[2.5]octa-5,7-dien-4-ones, is presented.

References

1. Isolation of 1–3: (a) W. A. Ayer and M. H. Saeedi-Ghomi, Can. J. Chem., 1981, 59, 2536; (b) O. Sterner, T. Anke, W. S. Sheldrick and W. Steglich, Tetrahedron, 1990, 46, 2389; (c) J.-L. Xie, L.-P. Li and Z.-Q. Dai, J. Org. Chem., 1992, 57, 2313Isolation of other sterpuranes: (d) C. Abell and A. P. Leech, Tetrahedron Lett., 1987, 28, 4887; (e) G. Cimino, A. D. Giulio, S. D. Rosa and S. D. Stefano, Tetrahedron, 1989, 45, 6479; (f) W. A. Ayer and L. M. Browne, Tetrahedron, 1981, 37, 2199.
2. 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.
3. 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).
4. (a) For excellent review on polyquinane natural products: G. Mehta and A. Srikrishna, Chem. Rev., 1997, 97, 671 and references cited therein; (b) R. D. Little, Chem. Rev., 1996, 96, 93; (c) V. Singh and B. Thomas, Tetrahedron, 1998, 54, 3647; (d) L. A. Paquette, Top. Curr. Chem., 1984, 119, 1.
5. 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.
6. (a) Y. Murata, T. Ohtsuka, H. Shirahama and T. Matsumoto, Tetrahedron Lett., 1981, 22, 4313; (b) L. Moens, M. M. Baizer and R. D. Little, J. Org. Chem., 1986, 51, 4497; (c) L. A. Paquette, H.-S. Lin, B. P. Gunn and M. J. Coghlan, J. Am. Chem. Soc., 1988, 110, 5818; (d) S.-K. Zhao and P. Helquist, J. Org. Chem., 1990, 55, 5820; (e) G. M. Strunz, R. Bethell, M. T. Dumas and N. Boyonoski, Can. J. Chem., 1997, 75, 742; (f) O. J. Birkenes, T. V. Hansen, S. M'dachi, L. Skattebol and Y. Stenstrom, Acta. Chem. Scand., 1998, 52, 806; (g) R. A. Gibbs, K. Bartels, R. W. K. Lee and W. H. Okamura, J. Am. Chem. Soc., 1989, 111, 3717; (h) N. Krause, Liebigs Ann. Chem., 1993, 521; (i) A. Arnone, C. D. Gregorio, G. Nasini and O. V. D. Pava, J. Chem. Soc., Perkin Trans. 1, 1997, 1523.
7. V. Singh, Acc. Chem. Res., 1999, 32, 324.
8. 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.
9. H. E. Zimmerman and D. Armesto, Chem. Rev., 1996, 96, 3065.
10. K. Tsubaki, T. Otsubo, K. Tanaka, K. Fuji and T. Kinoshita, J. Org. Chem., 1998, 63, 3260.
11. 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.
12. 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.
13. For synthesis of tetracyclic systems of type 16 by meta-photocycloaddition, P. A. Wender and J. J. Howbert, Tetrahedron Lett., 1982, 23, 3983.
14. E. J. Enholm and Z. J. Jia, J. Org. Chem., 1997, 62, 174.
15. 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.