Stereoselective synthesis of the bicyclic core structure of the highly oxidised sesquiterpene neoliacinic acid

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5605-5608

  Clark, J Stephen ^a   Dossetter, Alexander G ^a   Whittingham, William G ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SESQUITERPENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01136-7     Document Type: Article

References (27)

1. 1. Takaoka, D.; Nozaki, H.; Nakayama, M. J. Chem. Soc., Chem. Commun., 1987, 1861.
2. 2. Nozaki, H.; Hiroi, M.; Takaoka, D.; Nakayama, M. J. Chem. Soc., Chem. Commun., 1983, 1107.
3. 3. For recent reviews concerning C-H-insertion and ylide-forming reactions of metal carbenoids, see: Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091. Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, Chapter 5.1, pp 421-468.
4. 3. For recent reviews concerning C-H-insertion and ylide-forming reactions of metal carbenoids, see: Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091. Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, Chapter 5.1, pp 421-468.
5. 3. For recent reviews concerning C-H-insertion and ylide-forming reactions of metal carbenoids, see: Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091. Doyle, M. P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, Chapter 5.1, pp 421-468.
6. 4. For examples of the [2,3]-sigmatropic rearrangement of oxonium ylides generated from rhodium carbenoids, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc., 1986, 108, 6060.
7. (b) Johnson, C. R.; Roskamp, E. J. J. Am. Chem. Soc., 1986, 108, 6062.
8. 5. For examples of the [2,3]-sigmatropic rearrangement of oxonium ylides generated from copper carbenoids, see: Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385. Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381.
9. 5. For examples of the [2,3]-sigmatropic rearrangement of oxonium ylides generated from copper carbenoids, see: Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385. Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381.
10. 5. For examples of the [2,3]-sigmatropic rearrangement of oxonium ylides generated from copper carbenoids, see: Clark, J. S. Tetrahedron Lett. 1992, 33, 6193. Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385. Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381.
11. 6. For examples of the construction of substituted tetrahydrofurans by intramolecular C-H-insertion of rhodium carbenoids, see: Adams, J.; Poupart, M-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett., 1989, 30, 1749. Adams, J.; Poupart, M.-A.; Grenier, L. Tetrahedron Lett., 1989, 30, 1753. Spero, D. M.; Adams, J. Tetrahedron Lett., 1992, 33, 1753. Ye, T.; McKervey, M. A. Tetrahedron Lett., 1994, 35, 7269. Taber, D. F.; Song, Y. Tetrahedron Lett., 1995, 36, 2587.
12. 6. For examples of the construction of substituted tetrahydrofurans by intramolecular C-H-insertion of rhodium carbenoids, see: Adams, J.; Poupart, M-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett., 1989, 30, 1749. Adams, J.; Poupart, M.-A.; Grenier, L. Tetrahedron Lett., 1989, 30, 1753. Spero, D. M.; Adams, J. Tetrahedron Lett., 1992, 33, 1753. Ye, T.; McKervey, M. A. Tetrahedron Lett., 1994, 35, 7269. Taber, D. F.; Song, Y. Tetrahedron Lett., 1995, 36, 2587.
13. 6. For examples of the construction of substituted tetrahydrofurans by intramolecular C-H-insertion of rhodium carbenoids, see: Adams, J.; Poupart, M-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett., 1989, 30, 1749. Adams, J.; Poupart, M.-A.; Grenier, L. Tetrahedron Lett., 1989, 30, 1753. Spero, D. M.; Adams, J. Tetrahedron Lett., 1992, 33, 1753. Ye, T.; McKervey, M. A. Tetrahedron Lett., 1994, 35, 7269. Taber, D. F.; Song, Y. Tetrahedron Lett., 1995, 36, 2587.
14. 6. For examples of the construction of substituted tetrahydrofurans by intramolecular C-H-insertion of rhodium carbenoids, see: Adams, J.; Poupart, M-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett., 1989, 30, 1749. Adams, J.; Poupart, M.-A.; Grenier, L. Tetrahedron Lett., 1989, 30, 1753. Spero, D. M.; Adams, J. Tetrahedron Lett., 1992, 33, 1753. Ye, T.; McKervey, M. A. Tetrahedron Lett., 1994, 35, 7269. Taber, D. F.; Song, Y. Tetrahedron Lett., 1995, 36, 2587.
15. 6. For examples of the construction of substituted tetrahydrofurans by intramolecular C-H-insertion of rhodium carbenoids, see: Adams, J.; Poupart, M-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett., 1989, 30, 1749. Adams, J.; Poupart, M.-A.; Grenier, L. Tetrahedron Lett., 1989, 30, 1753. Spero, D. M.; Adams, J. Tetrahedron Lett., 1992, 33, 1753. Ye, T.; McKervey, M. A. Tetrahedron Lett., 1994, 35, 7269. Taber, D. F.; Song, Y. Tetrahedron Lett., 1995, 36, 2587.
16. 7. For examples of the synthesis of bridged bicyclic ethers by [1,2]-Stevens rearrangement of oxonium ylides generated from rhodium carbenoids, see: West, F. G.; Eberlein, T. H.; Tester, R. W. Perkin Trans. 1, 1993, 2857.
17. 8. For a study concerning the addition of organometallic reagents to (R)-isopropylideneglyceraldehyde, see: Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun., 1985, 1636.
18. 9. For the purposes of this model study, the two diastereoisomers of the allyl ether 7 were not separated. As a consequence of this, the enantiomeric purity of the aldehyde 8 was approximately 60% ee.
19. 10. For methods available for the preparation of α-diazo ketones from carboxylic acid derivatives, see: Regitz, M.; Mass, G. Diazo Compounds Properties and Synthesis; Academic Press: Orlando, 1986; Chapter 14, pp 436-533. Clark, J. S. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 3, Chapter 3.12, pp 443-490.
20. 10. For methods available for the preparation of α-diazo ketones from carboxylic acid derivatives, see: Regitz, M.; Mass, G. Diazo Compounds Properties and Synthesis; Academic Press: Orlando, 1986; Chapter 14, pp 436-533. Clark, J. S. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 3, Chapter 3.12, pp 443-490.
21. 11. Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett., 1992, 33, 2709. Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Commun., 1992, 1508.
22. 11. Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett., 1992, 33, 2709. Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Commun., 1992, 1508.
23. 3 to cyclic ketones, see: (a) Laemmle, J. T.; Ashby, E. C.; Roling, P. V. J. Org. Chem., 1973, 38, 2526.
24. (b) Ashby, E. C.; Laemmle, J. T. Chem. Rev., 1975, 75, 536.
25. (c) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc., 1989, 111, 6666.
26. 3 to cyclic ketones [ref. 12(c)]. (equation presented)
27. 3) δ 212.0 (s), 169.4 (s), 135.8 (d), 127.9 (d), 89.7 (s), 81.4 (d), 79.2 (d), 40.6 (t), 39.9 (t), 36.2 (t), 23.1 (q), 22. 4 (q), 20.8 (t).