A general approach to cyathin diterpenes. Total synthesis of allocyathin B3

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2125-2127

  Ward, Dale E ^a   Gai, Yuanzhu ^a   Qiao, Qi ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CYATHINS; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMISTRY; MEDICINAL PLANT; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, THIN LAYER; DITERPENES; INDICATORS AND REAGENTS; PLANTS, MEDICINAL;

EID: 0034644005     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006026c     Document Type: Article

References (43)

1. (a) Allbutt, A. D.; Ayer, W. A.; Brodie, H. J.; Johri, B. N.; Taube, H. Can. J. Microbiol. 1971, 17, 1401.
2. (b) Ayer, W. A.; Taube, H. Tetrahedron Lett. 1972, 19, 1917.
3. (c) Ayer, W. A.; Taube, H. Can. J. Chem. 1973, 51, 3842.
4. (d) Ayer, W. A.; Carstens, L. L. Can. J. Chem. 1973, 57, 3157.
5. (e) Ayer, W. A.; Browne, L. M.; Mercer, J. R.; Taylor, D. R.; Ward, D. E. Can. J. Chem. 1978, 56, 717.
6. (f) Ayer, W. A.; Yoshida, T.; Van Schie, D. M. J. Can. J. Chem. 1978, 50, 2113.
7. (g) Ayer, W. A.; Lee, S. P. J. Can. J. Chem. 1979, 57, 3332.
8. 1,2, 3,4-epoxide, C-1 ketone, C-2 ketone, C-1 β-OH, C-19 OH, C-19 acid.
9. For example, C-15 aldehyde, C-14 β-OH.
10. Hecht, H.-J.; Höfle, G.; Steglich, W.; Anke, T.; Oberwinkler, F. J. Chem. Soc., Chem. Commun. 1978, 665.
11. (a) Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569.
12. (b) Kawagishi, H.; Shimada, A.; Shizuki, K.; Mori, H.; Okamoto, K.; Sakamoto, H.; Furukawa, S. Heterocycl. Commun. 1996, 2, 51.
13. (c) Kawagishi, H.; Shimada, A.; Hosokawa, S.; Mori, H.; Sakamoto, H.; Ishiguro, Y.; Sakemi, S.; Bordner, J.; Kojima, N.; Furukawa, S. Tetrahedron Lett. 1996, 37, 7399.
14. Shibata, H.; Tokunaga, T. Karasawa, D.; Hirota, A. Nakayama, M.; Nozaki, H.; Tada, T. Agric. Biol. Chem. 1989, 53, 3373.
15. (a) Ohta, T.; Kita, T.; Kobayashi, N.; Obara, Y.; Nakahata, N.; Ohizumi, Y.; Takaya, Y.; Oshima, Y. Tetrahedron Lett. 1998, 39, 6229.
16. (b) Kita, T.; Takaya, Y.; Oshima, Y.; Aizawa, K.; Hirano, T.; Inakuma, T. Tetrahedron 1998, 54, 11877.
17. (a) Ayer, W. A.; Browne, L. M.: Fernandez, S.; Ward, D. E.; Yoshida, T. Rev. Latinoamer. Quim. 1978, 9, 177.
18. (b) Ayer. W. A.; Ward, D. E.; Browne, L. M.; Delbaere, L. T. J.; Hoyano, Y. Can. J. Chem. 1981, 59, 2665.
19. (c) Ward, D. E. Can. J. Chem. 1987, 65, 2380.
20. (d) Dahnke, K. R.; Paquette, L. A. J. Org. Chem. 1993, 59, 885.
21. (e) Piers, E.; Cook, K. L. Chem. Commun. 1996, 1879.
22. (f) Magnus, P.; Shen, L. Tetrahedron 1999, 55, 3553.
23. (g) Wright, D. L.; Whitehead, C. R.; Sessions, E. H.; Ghiviriga, I.; Frey, D. A. Org. Lett. 1999, 1, 1535.
24. (a) Snider, B. B.; Vo, N. H.; O'Neil, S. V.; Foxman, B. M. J. Am. Chem. Soc. 1996, 118, 7644.
25. (b) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732.
26. Tori, M.; Toyoda, N. Sono, M. J. Org. Chem. 1998, 63, 306.
27. After this paper was submitted, the synthesis of (±)-sarcodonin G, which has a trans 6-7 ring fusion and a C-19 hydroxyl group, was reported. Piers, E.; Gilbert, M.: Cook, K. L. Org. Lett. 2000, 2, 1407.
28. Rodriguez, J.: Dulcere, J.-P. Synthesis 1993, 1177.
29. Giese, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. L.; Trach, F. Org. React. 1996, 48, 301.
30. 3C-9 on irradiation of the C-2 methoxy group.
31. Several examples of this route to 3-methylenetetrahydrofurans can be found in ref 13. For early examples, see: (a) Okabe, M.; Abe, M.; Tada, M. J. Org. Chem. 1982, 47, 1775.
32. (b) Moriya, O.; Okawara, M.; Ueno, Y. Chem. Lett. 1984, 1437.
33. Sirkrishna, A.; Pullaiah, K. C. Tetrahedron Lett. 1987, 28, 5203.
34. 5 (ref 1e).
35. 2C-19 and HC-18 (8, 10.5 Hz) and chemical shift of the C-20 methyl group (δ 1.32) compared to those of 14 (and 18a). These coupling constants are consistent with the dihedral angles (-36°, -161°) for 15 determined by molecular mechanics (CaChe, version 3.9) which also indicated that 15 was 1.3 kcal/mol more stable than 18a. (19) For an example of unusually facile cyclization of a 1,4-diol, see: Schlessinger, R. H.; Schultz, J. A. J. Org. Chem. 1983, 48, 407.
36. Classon, B.; Liu, Z. J. Org. Chem. 1988, 53, 6126.
37. The presence of the transannular acetal within the seven-membered ring makes the cis-fused diastereomer impossibly strained.
38. For a review on oxidation with tetrapropylammonium perruthenate/ N-methylmorpholine N-oxide, see: Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
39. Stang, P. J.; Treptow, W. Synthesis 1980, 283.
40. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
41. For a review on the preparation and reactions of enol triflates, see: Ritter, K. Synthesis 1993, 735.
42. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109.
43. Ayer, W. A.; Nakashima, T. T.; Ward, D. E. J. Can. J. Chem. 1978, 56, 2197.