Abstract
The process of allylic transposition in SE' reactions is a significant construct for synthesis. The flexibility of a variety of allylation strategies provides for the rational design of pathways to a diverse array of complex targets. Our recent studies of SE' reactions will examine issues of stereoselectivity and efficiency in the context of applications toward the synthesis of marine natural products such as the xenicane diterpenes, which feature the strained E-cyclononene ring system, and peloruside A, a 16-membered macrocyclic lactone.
Conference
International Conference on Organic Synthesis (ICOS 17), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 17th, Daejeon, Korea, 2008-06-22–2008-06-27
References
1. (a) doi:10.1021/ja005644l, amphidinolide K: D. R. Williams, K. G. Meyer. J. Am. Chem. Soc. 123, 765 (2001);Search in Google Scholar
1. (b) doi:10.1002/anie.200351817, leucascandrolide A: D. R. Williams, S. V. Plummer, S. Patnaik. Angew. Chem., Int. Ed. 42, 3934 (2003);Search in Google Scholar
1. (c) doi:10.1073/pnas.0402477101, phorboxazole A: D. R. Williams, A. A. Kiryanov, U. Emde, M. P. Clark, M. A. Berliner, J. T. Reeves. Proc. Natl. Acad. Sci. USA 101, 12058 (2004);Search in Google Scholar
1. (d) doi:10.1016/S0040-4039(02)00907-3, laulimalide; D. R. Williams, L. Mi, R. J. Mullins, R. E. Stites. Tetrahedron Lett. 43, 4841 (2002);Search in Google Scholar
1. (e) deoxyneodolabelline: D. R. Williams, R. W. Heidebrecht Jr. J. Am. Chem. Soc. 125, 1843 (2003);10.1021/ja0279803Search in Google Scholar PubMed
1. (f) S. R. Chemler, W. R. Roush. Recent Applications of the Allylation Reaction to the Synthesis of Natural Products. Modern Carbonyl Chemistry, J. Otera (Ed.), pp. 403-490, Wiley-VCH (2000).10.1002/9783527613267.ch11Search in Google Scholar
2. G. Guella, F. Pietra. Chem. Commun. 1539 (1993).10.1039/c39930001539Search in Google Scholar
3. doi:10.1246/cl.1982.1927, Earlier studies had described 1 as a semi-synthetic derivative obtained from the diterpenoid, fukurinolal: M. Ochi, N. Masui, H. Kotsuki, I. Miura, T. Tokoroyama. Chem. Lett. 1927 (1982).Search in Google Scholar
4. doi:10.1021/jo01326a040, J. Finer, J. Clardy, W. Fenical, L. Minale, R. Riccio, J. Battaile, M. Kirkup, R. E. Moore. J. Org. Chem. 44, 2044 (1979).Search in Google Scholar
5. doi:10.1021/ja00459a040, D. J. Vanderah, P. A. Steudler, L. S. Clereszko, F. J. Schmitz, J. D. Ekstrand, D. van der Helm. J. Am. Chem. Soc. 99, 5780 (1977).Search in Google Scholar
6. doi:10.1016/S0040-4039(00)99187-1, I. Ohtani, T. Kusumi, M. O. Ishitsuka, H. Kakisawa. Tetrahedron Lett. 30, 3147 (1989).Search in Google Scholar
7. doi:10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N, For a review: S. R. Chemler, D. Trauner, S. J. Danishefsky. Angew. Chem., Int. Ed. 40, 4544 (2001).Search in Google Scholar
8. doi:10.1021/ja01057a040, E. J. Corey, R. B. Mitra, H. Uda. J. Am. Chem. Soc. 86, 485 (1964).Search in Google Scholar
9. doi:10.1021/ja8003705, O. V. Larionov, E. J. Corey. J. Am. Chem. Soc. 130, 2954 (2008).Search in Google Scholar
10. doi:10.1002/anie.200600641, A. Gradillas, J. Perez-Castells. Angew. Chem., Int. Ed. 45, 6086 (2006).Search in Google Scholar
11. doi:10.1021/jo070862j, L. A. Paquette, S. Dong, G. D. Parker. J. Org. Chem. 72, 7135 (2007).Search in Google Scholar
12. J. Mann, A. C. Weymouth-Wilson. Org. Synth. 75, 139 (1997).Search in Google Scholar
13. doi:10.1055/s-1992-26080, P. Cintas. Synthesis 3, 248 (1992).Search in Google Scholar
14. (a) H. Yamamoto. "Propargyl and allenyl organometallics", in Comp. Org. Synth. B. M. Trost, I. Fleming (Eds.), pp. 81-98, Pergamon Press (1991);10.1016/B978-0-08-052349-1.00025-1Search in Google Scholar
14. (b) H. Hopf, I. Bohm, J. Kleinschroth. Org. Syn. Coll. 7, 485 (1990).Search in Google Scholar
15. doi:10.1021/jo00219a058, B. L. Chenard, L. F. Davidson, T. V. Rajanbabu. J. Org. Chem. 50, 3667 (1985).Search in Google Scholar
16. D. R. Williams. Synthesis Studies of Dolabellane and Transannular Processes Leading to Related Diterpenes in Strategies and Tactics in Organic Synthesis, M. Harmata (Ed.), Vol. 7, pp. 243-267, Elsevier (2008).10.1016/S1874-6004(08)80011-1Search in Google Scholar
17. doi:10.1002/hlca.19940770503, G. Guella, G. Chiasera, I. N'Diaye, F. Pietra. Helv. Chim. Acta 77, 1203 (1994).Search in Google Scholar
18. D. R. Williams, P. P. Nag, N. Zorn. Curr. Opin. Drug Discov. Dev. 11, 251 (2008).Search in Google Scholar
19. doi:10.1021/jo991296y, L. M. West, P. T. Northcote, C. N. Battershill. J. Org. Chem. 65, 445 (2000).Search in Google Scholar
20. (a) doi:10.1002/anie.200351145, X. Liao, Y. Wu, J. K. DeBrabander. Angew Chem., Int. Ed. 42, 1648 (2003);Search in Google Scholar
20. (b) doi:10.1021/ol050070g, M. Jin, R. E. Taylor. Org. Lett. 7, 1303 (2005);Search in Google Scholar
20. (c) doi:10.1021/ol703091b, A. K. Ghosh, X. Xu, J.-H. Kim, C.-X. Xu. Org. Lett. 10, 1001 (2008).Search in Google Scholar
21. doi:10.1021/ja0580237, J. Jimenez-Barbero, A. Canales, P. T. Northcote, R. M. Buey, J. M. Andreu, J. F. Diaz. J. Am. Chem. Soc. 128, 8757 (2006).Search in Google Scholar
22. (a) doi:10.1021/ja00196a082, E. J. Corey, C.-M. Yu, S. S. Kim. J. Am. Chem. Soc. 111, 5495 (1989);Search in Google Scholar
22. (b) doi:10.1016/S0040-4039(98)01557-3, D. R. Williams, D. A. Brooks, K. G. Meyer, M. P. Clark. Tetrahedron Lett. 39, 7251 (1998);Search in Google Scholar
22. (c) doi:10.1139/v03-168, D. R. Williams, K. G. Meyer, K. Shamim, S. Patnaik. Can. J. Chem. 82, 120 (2004).Search in Google Scholar
23. doi:10.1021/jo00067a002, G. A. Crispino, K.-S. Jeong, H. C. Kolb, Z.-M. Wang, D. Xu, K. B. Sharpless. J. Org. Chem. 58, 3785 (1993).Search in Google Scholar
24. (a) doi:10.1021/jo00160a046, K. Tamao, N. Ishida, M. Kumada. J. Org. Chem. 48, 2122 (1983);Search in Google Scholar
24. (b) doi:10.1021/ol0359259, D. L. Aubele, C. A. Lee, P. E. Floreancig. Org. Lett. 5, 4521 (2003);Search in Google Scholar
24. (c) doi:10.1016/j.tet.2005.12.005, C. Perez-Balado, I. E. Marko. Tetrahedron 62, 2331 (2006).Search in Google Scholar
25. (a) doi:10.1002/chem.200600251, C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ. Chem.Eur. J. 12, 4743 (2006);Search in Google Scholar
25. (b) doi:10.1002/chem.200600206, M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente. Chem.Eur. J. 12, 4749 (2006).Search in Google Scholar
26. (a) doi:10.1021/jo951313t, K. S. Ravikumar, S. Chandrasekaran. J. Org. Chem. 61, 826 (1996);Search in Google Scholar
26. (b) doi:10.1021/jo9902906, K. S. Ravikumar, S. Sinha, S. Chandrasekaran. J. Org. Chem. 64, 5841 (1999).Search in Google Scholar
27. doi:10.1016/S0040-4039(00)85909-2, W. C. Still, C. Gennari. Tetrahedron Lett. 24, 4405 (1983).Search in Google Scholar
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