G.L. Morgans et al. / Tetrahedron 65 (2009) 10650–10659
10659
Anderluh, P. S.; Dolenc, M. S.; Kikelj, D. Tetrahedron 2005, 61, 7325–7348; (d)
Achari, B.; Mandal, S. B.; Dutta, P. K.; Chowdhury, C. Synlett 2004, 2449–2467.
2. Wu, J.-H.; Chang, F.-R.; Hayashi, K.-i.; Shiraki, H.; Liaw, C.-C.; Nakanishi, Y.;
Bastow, K. F.; Yu, D.; Chen, I.-S.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2003, 13,
2223–2225.
3. (a) Debenedetti, S. L.; Nadinic, E. L.; Coussio, J. D.; De Kimpe, N.; Feneau-Du-
pont, J.; Declercq, J. P. Phytochemistry 1991, 30, 2757–2758; (b) Of interest is that
a closely related compound purpurasol, the 5-demethoxy derivative of pur-
purenol, has also been isolated. A revised structure of this compound, con-
cerning the substituted dioxane portion, has also been published and we thank
a reviewer for pointing out this matter: Boeykens, M.; De Kimpe, N.; Debene-
detti, S. L.; Nadinic, E. L.; Gomez, M. A.; Coussio, J. D.; Abyshev, A. Z.; Gindin, V.
A. Phytochemistry 1994, 36, 1559–1560.
17. Blouin, M.; Frenette, R. J. Org. Chem. 2001, 66, 9043–9045.
18. Clavier, S.; Khouili, M.; Bouyssou, P.; Coudert, G. Tetrahedron 2002, 58, 1533–
1540.
19. For another approach involving the RCM of two aryl vinyloxy functionalities
see: Leriche, P.; Blanchard, P.; Fre`re, P.; Levillain, E.; Mabon, G.; Roncali, J. Chem.
Commun. 2006, 275–277.
20. See for example: (a) Pathak, R.; Naiker, P.; Thompson, W. A.; Fernandes, M. A.;
de Koning, C. B.; van Otterlo, W. A. L. Eur. J. Org. Chem. 2007, 5337–5345; (b)
Govender, S.; Mmutlane, E.; van Otterlo, W. A. L.; de Koning, C. B. Org. Biomol.
Chem. 2007, 5, 2433–2440; (c) van Otterlo, W. A. L.; Pathak, R.; de Koning, C. B.;
Fernandes, M. A. Tetrahedron Lett. 2004, 45, 9561–9563; (d) de Koning, C. B.;
van Otterlo, W. A. L.; Michael, J. P. Tetrahedron 2003, 59, 8337–8345.
21. For excellent reviews on transition metal catalyzed isomerizations see the next
two references: (a) Krompiec, S.; Krompiec, M.; Penczek, R.; Ignasiak, H. Coord.
Chem. Rev. 2008, 252, 1819–1841; (b) Kuz´nik, N.; Krompiec, S. Coord. Chem. Rev.
´
4. Thiery, V.; Coudert, G.; Bizot-Espiard, J.-G.; Pfeiffer, B.; Renard, P.; Lindenbaum,
A.; Guillaumet, G. J. Med. Chem. 2001, 44, 3904–3914.
´
5. (a) Charton, I.; Mamai, A.; Bennejean, C.; Renard, P.; Howell, H. E.; Guardiola-
Lemaˆıtre, B.; Delagrange, P.; Morgan, P. J.; Viaud, M.-C.; Guillaumet, G. Bioorg.
Med. Chem. 2000, 8, 105–114; (b) Mamai, A.; Bennejean, C.; Renard, P.; Dela-
2007, 251, 222–233; (c) Krompiec, S.; Kuznik, N.; Urbala, M.; Rzepa, J. J. Mol.
Catal. 2006, 248, 198–209; (d) Krompiec, S.; Kuz´nik, N.; Krompiec, M.;
A
Penczek, R.; Mrzigod, J.; To´rz, A. J. Mol. Catal. A 2006, 253, 132–146; (e) Kuz´nik,
N.; Krompiec, S.; Bieg, T.; Baj, S.; Skutil, K.; Chrobok, A. J. Organomet. Chem.
2003, 665, 167–175.
ˆ
grange, P.; Guardiola-Lemaıtre, B.; Howell, H. E.; Viaud, M.-C.; Guillaumet, G.
Pharm. Pharmacol. Commun. 1999, 5, 199–206; (c) Charton, I.; Mamai, A.; Ben-
nejean, C.; Renard, P.; Delagrange, P.; Morgan, P. J.; Howell, H. E.; Gourdel-
Martin, M. E.; Viaud, M.-C.; Guillaumet, G. Pharm. Pharmacol. Commun. 2000, 6,
49–60.
6. Rybczynski, P. J.; Zeck, R. E.; Combs, D. W.; Turchi, I.; Burris, T. P.; Xu, J. Z.; Yang,
M.; Demarest, K. T. Bioorg. Med. Chem. Lett. 2003, 13, 2359–2362.
7. (a) Bergman, J.; Rosenzweig-Lipson, S.; Spealman, R. D. J. Pharmacol. Exp. Ther.
1995, 273, 40–48; (b) Spealman, R. D. J. Pharmacol. Exp. Ther. 1996, 278, 1128–
1137.
22. After the reaction was deemed complete by the 1H NMR spectra, any un-
saturated gases resulting from the metathesis reaction were allowed to diffuse
from the solvent before final 1H and 13C NMR spectroscopy was performed to
confirm the product structures. Where necessary the solvent was replaced with
CDCl3 to facilitate comparison with the literature data.
23. For recent representative examples describing an isomerization process fol-
lowed by RCM and related papers see: (a) Vik, A.; Gundersen, L.-L. Tetrahedron
Lett. 2007, 48, 1931–1934; (b) Martı
´nez-Estı´balez, U.; Sotomayor, N.; Lete, E.
8. Armenise, D.; Trapani, G.; Arrivo, V.; Laraspata, E.; Morlacchi, F. J. Heterocycl.
Chem. 2000, 37, 1611–1616.
Tetrahedron Lett. 2007, 48, 2919–2922; (c) Banaszak, E.; Comoy, C.; Fort, Y.
´
Tetrahedron Lett. 2006, 47, 6235–6238; (d) Jime
´nez-Gonza´lez, L.; Alvarez-Corral,
9. See for example: (a) Guillaumet, G.; Trumtel, M.; Coudert, G.; Zeggaf, C. Syn-
thesis 1986, 337–338; (b) Moreau, P.; Guillaumet, G.; Coudert, G. Synth. Com-
M.; Mun
˜oz-Dorado, M.; Rodrı´guez-Garcı´a, I. Chem. Commun. 2005, 2689–2691;
(e) Arisawa, M.; Terada, Y.; Theeraladanon, C.; Takahashi, K.; Nakagawa, M.;
`
´ ˇ
mun. 1994, 24, 1781–1787; (c) Chacun-Lefevre, L.; Buon, C.; Bouyssou, P.;
Nishida, A. J. Organomet. Chem. 2005, 690, 5398–5406; (f) Nunez, A.; Cuadro, A.
Coudert, G. Tetrahedron Lett. 1998, 39, 5763–5764; (d) Buon, C.; Chacun-Lefe`vre,
L.; Rabot, R.; Bouyssou, P.; Coudert, G. Tetrahedron 2000, 56, 605–614.
10. (a) RCM (for the synthesis of molecules with potential bio-activity): Panayides,
J.-L.; Pathak, R.; Panagiotopoulos, H.; Fernandes, M. A.; Davids, H.; de Koning, C.
B.; van Otterlo, W. A. L. Tetrahedron 2007, 63, 4737–4747; (b) Coyanis, E. M.;
Panayides, J.-L.; Fernandes, M. A.; de Koning, C. B.; van Otterlo, W. A. L. J. Or-
ganomet. Chem. 2006, 691, 5222–5239 RCM–redox isomerization: (c) Ring-
opening metathesis polymerization: Mamo, M. A.; Coville, N. J.; van Otterlo, W.
A. L. Fullerenes, Nanotubes, Carbon Nanostructures 2007, 15, 341–352; (d) RCM–
aromatization: Pelly, S. C.; Parkinson, C. J.; van Otterlo, W. A. L.; de Koning, C. B.
J. Org. Chem. 2005, 70, 10474–10481; (e) ene–yne RCM: van Otterlo, W. A. L.;
Ngidi, E. L.; de Koning, C. B.; Fernandes, M. A. Tetrahedron Lett. 2004, 45, 659–
662.
11. For a list of recent reviews on RCM see:the following reference and reviews
cited therein (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18–29; (b)
van Otterlo, W. A. L.; de Koning, C. B. Chem. Rev. 2009, 109, 3743–3782.
12. See, for example, the following recent papers and references cited therein: (a)
Scalzullo, S. M.; Ul Islam, R.; Morgans, G. L.; Michael, J. P.; van Otterlo, W. A. L.
Tetrahedron Lett. 2008, 49, 7403–7405; (b) Panayides, J.-L.; Pathak, R.; de
Koning, C. B.; van Otterlo, W. A. L. Eur. J. Org. Chem. 2007, 4953–4961; (c) Pa-
thak, R.; Panayides, J.-L.; Jeftic, T. D.; de Koning, C. B.; van Otterlo, W. A. L. S. Afr.
W. A. L.; Ngidi, E. L.; Kuzvidza, S.; Morgans, G. L.; Moleele, S. S.; de Koning, C. B.
Tetrahedron 2005, 61, 9996–10006; (e) van Otterlo, W. A. L.; Morgans, G. L.;
Madeley, L. G.; Kuzvidza, S.; Moleele, S. S.; Thornton, N.; de Koning, C. B. Tet-
rahedron 2005, 61, 7746–7755.
13. For an informative review exploring pre- and post-RCM–isomerization see: (a)
Schmidt, B. Eur. J. Org. Chem. 2004, 1865–1880; For a review on tandem pro-
cesses involving methesis see: (b) Dragutan, V.; Dragutan, I. J. Organomet. Chem.
2006, 691, 5129–5147.
14. For reviews describing the metathesis of heteroatom-substituted olefins and
examples relating to the metathesis of vinyl ethers, enamines and enamides
and vinyl sulfides see: (a) Brown, R. C. D.; Satcharoen, V. Heterocycles 2006, 70,
705–736; (b) Van de Weghe, P.; Bisseret, P.; Blanchard, N.; Eustache, J. J. Or-
ganomet. Chem. 2006, 691, 5078–5108.
15. Experimental data provided from the work of the following students: PhD:
Morgans, G. L.; MSc: Ngidi, E. L.; Madeley, L. G. Aderibigbe, B. A.; Honours
project: Khanye, S. D.
16. For a communication see: van Otterlo, W. A. L.; Ngidi, E. L.; de Koning, C. B.
Tetrahedron Lett. 2003, 44, 6483–6486.
M.; Alvarez-Builla, J.; Vaquero, J. J. Org. Lett. 2004, 6, 4125–4127; (g) Nguyen
Van, T.; De Kimpe, N. Tetrahedron Lett. 2004, 45, 3443–3446; For an example
involving the simultaneous use of catalysts 13 and 14 see: (h) Michalak, M.;
Wicha, J. Synlett 2005, 2277–2280.
24. The synthesis of N-substituted 1,4-dihydroquinoxalines was also attempted,
without success, applying this methodology (see next reference) and using
the following amine protecting groups: Ts, Boc, COPh and COMe. In all cases the
synthetic sequence was successful until the isomerization step, after which the
metathesis reaction only provided recovered starting material.
25. For a communication see: van Otterlo, W. A. L.; Morgans, G. L.; Khanye, S. D.;
Aderibigbe, B. A. A.; Michael, J. P.; Billing, D. G. Tetrahedron Lett. 2004, 45, 9171–
9175.
26. For an example where a benzoxazine was formed in a methylenation–RCM
strategy in the presence of benzoquinone, see: Bennasar, M. L.; Roca, T.;
´
´
Monerris, M.; Garcıa-Dıaz, D. J. Org. Chem. 2006, 71, 7028–7034.
27. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239–
2258.
28. See for example: (a) Liu, Z.; Ranier, J. D. Org. Lett. 2005, 7, 131–133; (b) Ka-
tayama, H.; Nagao, M.; Ozawa, F. Organometallics 2003, 22, 586–593; (c) Ka-
tayama, H.; Urushima, H.; Nishioka, T.; Wada, C.; Nagao, M.; Ozawa, F. Angew.
Chem., Int. Ed. 2000, 39, 4513–4515; (d) Katayama, H.; Urushima, H.; Ozawa, F.
Chem. Lett. 1999, 369–370.
29. Uchida, M.; Otsubo, K.; Matsubara, J.; Ohtani, T.; Morita, S.; Yamasaki, K. Chem.
Pharm. Bull. 1995, 43, 693–698.
30. Price, C. C.; Snyder, W. H. J. Am. Chem. Soc. 1961, 83 1773–1773.
31. Tarbell, D. S.; McCall, M. A. J. Am. Chem. Soc. 1952, 74, 48–56.
32. Boyd, D. R.; Sharma, N. D.; Haughey, S. A.; Kennedy, M. A.; Malone, J. F.;
Shepherd, S. D.; Allen, C. C. R.; Dalton, H. Tetrahedron 2004, 60, 549–559.
33. Parham, W. E.; Jones, J. D. J. Am. Chem. Soc. 1954, 76, 1068–1074.
34. Ranu, B. C.; Dutta, J.; Guchhait, S. K. J. Org. Chem. 2001, 66, 5624–5626.
35. Prajer-Janczeweska, L.; Wroblewski, J. Pol. J. Chem. 1978, 52, 1675–1682.
36. (a) Kashima, C.; Tomotake, A.; Omote, Y. J. Org. Chem. 1987, 52, 5616–5621; (b)
Dorrestijn, E.; Epema, O. J.; van Scheppingen, W. B.; Mulder, P. J. Chem. Soc.,
Perkin Trans. 2 1998, 1173–1178.
37. Sridhar, M.; Kumar, B. A.; Narender, R. Tetrahedron Lett. 1998, 39, 2847–2850.
38. Morgans, G. L.; Scalzullo, S. M.; Fernandes, M. A.; Michael, J. P.; van Otterlo, W.
A. L. Acta Crystallogr., Sect. C 2007, 63, o309–o311.
39. Potts, K. T.; Dery, M. O.; Juzukonis, W. A. J. Org. Chem. 1989, 54, 1077–1088.
40. Bartsch, H.; Ofner, M.; Schwarz, O.; Thomann, W. Heterocycles 1984, 22, 2789–
2797.