Total synthesis of the cyathane diterpenoid (±)-sarcodonin G

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1407-1410

  Piers, Edward ^a   Gilbert, Michael ^a   Cook, Katherine L ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; SARCODONIN G;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DITERPENES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 0034682162     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057333     Document Type: Article

References (40)

1. The numbering system shown in 1 is that proposed by Ayer and Taube (ref 2).
2. Ayer, W. A.; Taube, H. Tetrahedron Lett. 1972, 1917.
3. Ayer, W. A.; Lee, S. P. Can. J. Chem. 1979, 57, 3332, and earlier publications in the series.
4. (a) Shibata, H.; Tokunaga, T.; Karasawa, D.; Hirota, A.; Nakayama, M.: Nozaki, H.: Tada, T. Agric. Biol. Chem. 1989, 53, 3373.
5. (b) Kawagishi, H.; Shimada, A.; Shirai, R.; Okamoto, K.; Ojima, F.; Sakamoto, H.; Ishiguro, Y.; Furukawa, S. Tetrahedron Lett. 1994, 35, 1569.
6. (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.
7. (d) Toyota, M.; Nakaisi, E.; Asakawa, Y. Phytochemistry 1996, 43, 1057.
8. (e) Ohta, T.; Kita, T.; Kobayashi, N.; Obara, Y.; Nakahata, N.; Ohizuma, Y.; Takaya, Y.; Oshima, Y. Tetrahedron Lett. 1998, 39, 6229.
9. (f) Shibata, H.; Irie, A.; Morita, Y. Biosci., Biotechnol., Biochem. 1998, 62, 2450.
10. (g) Kita, T.; Takaya, Y.; Oshima, Y.; Ohta, T.; Aizawa, K.; Hirano, T.; Inakuma, T. Tetrahedron 1998, 54, 11877.
11. Allbutt, A. D.; Ayer, W. A.; Brodie, H. J.; Johri, B. N.; Taube, H. Can. J. Microbiol. 1971, 17, 1401.
12. Obara, Y.; Nakahata, N.; Kita, T.; Takaya, Y.; Kobayashi, H.; Hosoi, S.; Kiuchi, F.; Ohta, T.; Oshima, Y.; Ohizuma, Y. Eur. J. Pharmacol. 1999, 370, 79.
13. For completed syntheses, see: (a) Snider, B. B.; Vo, N. H.; O'Neil, S. V.; Foxman, B. M. J. Am. Chem. Soc. 1996, 118, 7644.
14. (b) Snider, B. B.; Vo, N. H.; O'Neil, S. V. J. Org. Chem. 1998, 63, 4732.
15. (c) Tori, M.; Toyoda, N.; Sono, M. J. Org. Chem. 1998, 63, 306.
16. For synthetic approaches, see: (a) Ayer, W. A.; Ward, D. E.; Browne, L. M.; Delbaere, L. T. J.; Hoyano, Y. Can. J. Chem. 1981, 59, 2665.
17. (b) Ward, D. E. Can. J. Chem. 1987, 65, 2380.
18. (c) Dahnke, K. R.; Paquette, L. A. J. Org. Chem. 1994, 59, 885.
19. (d) Magnus, P.; Shen, L. Tetrahedron 1999, 55, 3553.
20. (e) Wright, D. L.; Whitehead, C. R.; Sessions, E. H.; Ghiviriga, I.; Frey, D. A. Org. Lett. 1999, 1, 1535.
21. Piers, E.; Lemieux, R. M. Organometallics 1998, 17, 4213.
22. All new compounds reported herein that were isolated and purified exhibited spectra in accord with assigned structures and gave satisfactory elemental (C, H) combustion analyses and/or molecular mass determinations (high-resolution mass spectrometry).
23. For a report on the stereospecific deconjugation of alkyl (E)-and (Z)-3-trimethylstannylalk-2-enoates, see: Piers, E.; Gavai, A. V. J. Org. Chem. 1990, 55, 2374.
24. Dormoy, J.-R.; Castro, B. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.-in-Chief; John Wiley & Sons: Chichester, Vol. 8, 1995; p 5393.
25. Piers, E.; Yeung, B. W. A.; Fleming, F. F. Can. J. Chem. 1993, 71, 280.
26. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794.
27. Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1337.
28. Stork, G.; Benaim, J. J. Am. Chem. Soc. 1971, 93, 5938.
29. Piers, E.; Kaller, A. M. Tetrahedron Lett. 1996, 37, 5857.
30. (a) Piers, E.; Marais, P. C. Tetrahedron Lett. 1985, 29, 4053.
31. (b) Piers E.; Cook, K. L. J. Chem. Soc., Chem. Commun. 1996, 1879.
32. Still, W. C.; Mitra, A. J. Am. Chem. Soc. 1978, 100, 1927.
33. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
34. Alderdice, M.; Sum, F. W.; Weiler, L. Org. Synth. 1990, 62, 14.
35. Clark, J. H.; Miller, J. M. J. Chem. Soc., Perkin Trans. 1 1977, 1743.
36. Hasegawa, E.; Kitazume, T.; Suzuki, K.; Tosaka, E. Tetrahedron Lett. 1998, 39, 4059.
37. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
38. Williams, D. R.; Nishitani, K. Tetrahedron Lett. 1980, 21, 4417.
39. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
40. 3: 316.2039. Found (HRMS): 316.2038. These data agree well with those reported for the natural product (ref 4a).