Asymmetric total synthesis of (+)-luciduline: Toward a general approach to related lycopodium alkaloids

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5354-5362

  Barbe, Guillaume ^a,c   Fiset, Dominic ^a   Charette, André B ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

^c NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2-DIHYDROPYRIDINE; ALKENE METATHESIS; ASYMMETRIC SYNTHESIS; ASYMMETRIC TOTAL SYNTHESIS; DERIVATIZATIONS; DIELS-ALDER CYCLOADDITIONS; GENERAL APPROACH; KEY FEATURE; NATURAL PRODUCTS; RESEARCH PROGRAMS; SYNTHETIC APPROACH;

ALDEHYDES; CYCLOADDITION; METABOLITES; NITROGEN COMPOUNDS; OLEFINS; PYRIDINE;

SYNTHESIS (CHEMICAL);

11 TERT BUTYL 6 ETHYL 3 METHYL 7 OXODECAHYDRO 1H 1,8 (EPIMINOMETHANO)BENZO[7]ANNULENE 6,11 DICARBOXYLATE; 11 TERT BUTYL 6 ETHYL 7 HYDROXY 3 METHYLDECAHYDRO 1H 1,8 (EPIMINOMETHANO)BENZO[7]ANNULENE 6,11 DICARBOXYLATE; 7 METHYLOCTAHYDRO 1,5,3 (AZANETRIYL METHANO)NAPHTHALEN 2(1H)ONE; ACROLEIN; ALKALOID; ALKALOID DERIVATIVE; BENZYL 3 ACETYL 7 METHYL 5 OXOOCTAHYDROQUINOLINE 1(2H)CARBOXYLATE; BENZYL 3 ETHENYL 5 HYDROXY 3,4,4A,5,6,8A HEXAHYDROQUINOLINE 1(2H)CARBOXYLATE; BENZYL 3 ETHENYL 5 OXO 3,4,4A,5,6,8A HEXAHYDROQUINOLINE 1(2H)CARBOXYLATE; BENZYL 3 ETHENYL 7 METHYL 5 OXOOCTAHYDROQUINOLINE 1(2H)CARBOXYLATE; BENZYL 3 METHYL 6 OXO 1,2,3,4,6,7,8,8A OCTAHYDRO 1,7 (EPIMINOMETHANO)NAPHTHALENE 10 CARBOXYLATE; BENZYL 5 ([TERT BUTYL(DIMETHYL)SILYL]OXY) 3 ETHENYL 3,4,4A,5,6,8A HEXAHYDROQUINOLINE 1(2H) CARBOXYLATE; BENZYL 7 (1 ([TERT BUTYL(DIMETHYL)SILYL]OXY)BUT 3 EN 1YL) 2 AZABICYCLO[2.2.2]OCT 5 ENE 2 CARBOXYLATE; BENZYL 7 (1 HYDROXYBUT 3 EN 1 YL) 2 AZABICYCLO[2.2.2]OCT 5 ENE 2 CARBOXYLATE; BENZYL 7 (HYDROXYMETHYL) 2 AZABICYCLO[2.2.2]OCT 5 ENE 2 CARBOXYLATE; BENZYL 7 FORMYL 2 AZABICYCLO[2.2.2]OCT 5 ENE 2 CARBOXYLATE; BENZYL PYRIDINE 1(2H)CARBOXYLATE; DIHYDROLYCOLUCINE; LUCIDINE A; LUCIDULINE; LUCIDULINONE; LYCONADIN A; LYCONADIN B; NANKAKURINE A; NANKAKURINE B; OXOLUCIDINE A; SPIROLUCIDINE; TERT BUTYL 3 METHYL 6 OXODECAHYDRO 1,7 (EPIMINOMETHANO)NAPHTHALENE 10 CARBOXYLATE; TERT BUTYL 5 BROMO 3 METHYL 6 OXODECAHYDRO 1,7 (EPIMINOMETHANO)NAPHTHALENE 10 CARBOXYLATE; TERT UTYL 6 (1 DIAZO 2 ETHOXY 2 OXOETHYL) 6 HYDROXY 3 METHYLDECAHYDRO 1,7 (EPIMINOMETHANO) NAPHTHALENE 10 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; LYCOPODIUM; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; LYCOPODIUM; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM;

EID: 79959638884     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200745n     Document Type: Article

References (52)

1. For the isolation of the first Lycopodium alkaloid, lycopodine, see: Bödeker, K. Justus Liebigs Ann. Chem. 1881, 208, 363-367
2. For a recent review, se: e Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679-729
3. For recent examples of total syntheses of Lycopodium alkaloids, see: Yang, H.; Carter, R. G. J. Org. Chem. 2010, 75, 4929-4938
4. Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594-9595
5. Bisai, V.; Sarpong, R. Org. Lett. 2010, 12, 2551-2553
6. Fischer, D. L.; Sarpong, R. J. Am. Chem. Soc. 2010, 132, 5926-5927
7. Yuan, C.; Chang, C.; Axelrod, A.; Siegel, D. J. Am. Chem. Soc. 2010, 132, 5924-5925
8. Laemmerhold, K. M.; Breit, B. Angew. Chem., Int. Ed. 2010, 49, 2367-2370
9. DeLorbe, J. E.; Lotz, M. D.; Martin, S. F. Org. Lett. 2010, 12, 1576-1579
10. Nakamura, Y.; Burke, A. M.; Kotani, S.; Ziller, J. W.; Rychnovsky, S. D. Org. Lett. 2010, 12, 72-75 and references therein
11. For a recent review discussing Lycopodium alkaloids' biological activity, see: Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772
12. Nilsson, B. L.; Overman, L. E.; de Alaniz, J. R.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 11297-11299
13. Cheng, X.; Waters, S. P. Org. Lett. 2010, 12, 205-207
14. West, S. P.; Bisai, A.; Lim, A. D.; Narayan, R. R.; Sarpong, R. J. Am. Chem. Soc. 2009, 131, 11187-11194
15. Bisai, A.; West, S. P.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222-7223
16. For reported asymmetric total syntheses of luciduline, see: Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229-231
17. Oppolzer, W.; Petrzilka, M. Helv. Chim. Acta 1978, 61, 2755-2762 For the total syntheses of (±)-luciduline, see: Schumann, D.; Naumann, A. Liebigs Ann. Chem. 1984, 8, 1519-1528
18. Szychowsky, J.; MacLean, D. B. Can. J. Chem. 1979, 57, 1631-1637
19. Scott, W. L.; Evans, D. A. J. Am. Chem. Soc. 1972, 94, 4779-4780
20. Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 13873-13875 For examples with analogous all-carbon bicyclo[2.2.2]octene, see: Pfeiffer, M. W. B.; Phillips, A. J. J. Am. Chem. Soc. 2005, 127, 5334-5335
21. Minger, T. L.; Phillips, A. J. Tetrahedron Lett. 2002, 43, 5357-5359
22. For seminal application in total synthesis, see: Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855-856 For all-carbon systems, see: Hart, A. C.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 1094-1095
23. Holtsclaw, J.; Koreeda, M. Org. Lett. 2004, 6, 3719-3722
24. Wrobleski, A.; Sahasrabudhe, K.; Aubé, J. J. Am. Chem. Soc. 2004, 126, 5475-5481
25. Hagiwara, H.; Katsumi, T.; Endou, S.; Hoshi, T.; Suzuki, T. Tetrahedron 2002, 58, 6651-6654
26. Funel, J.; Prunet, J. Synlett 2005, 235
27. Stragies, R.; Blechert, S. Synlett 1998, 169-170 For oxygen-containing systems, see: Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829
28. Arjona, O.; Csaky, A. G.; Murcia, M. C.; Plumet, J. Tetrahedron Lett. 2000, 41, 9777-9779
29. Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640 For nitrogen-containing systems, see: Maechling, S.; Norman, S. E.; McKendrick, J. E.; Basra, S.; Koppner, K.; Blechert, S. Tetrahedron Lett. 2006, 47, 189-192
30. Liu, Z.; Rainier, J. D. Org. Lett. 2006, 8, 459-462
31. Arjona, O.; Csaky, A. G.; Medel, R.; Plumet, J. J. Org. Chem. 2002, 67, 1380-1383
32. Buchert, M.; Meinke, S.; Prenzel, A. H. G. P.; Deppermann, N.; Maison, W. Org. Lett. 2006, 8, 5553-5556
33. Satoh, N.; Akiba, T.; Yokoshima, S.; Fukuyama, T. Tetrahedron 2009, 65, 3239-3245
34. Satoh, N.; Akiba, T.; Yokoshima, S.; Fukuyama, T. Angew. Chem., Int. Ed. 2007, 46, 5734-5736
35. For enantioselective Diels-Alder reactions of dihydropyridines, see: Nakano, H.; Osone, K.; Takeshita, M.; Kwon, E.; Seki, C.; Matsuyama, H.; Takano, N.; Kohari, Y. Chem. Commun. 2010, 46, 4827-4829
36. Takenaka, N.; Huang, Y.; Rawal, V. H. Tetrahedron 2002, 58, 8299-8305
37. Nakano, H.; Tsugawa, N.; Fujita, R. Tetrahedron Lett. 2005, 46, 5677-5681 For diastereoselective reactions of chiral dihydropyridines, see: Mehmandoust, M.; Marazano, C.; Singh, R.; Gillet, B.; CMsario, M.; Fourrey, J.-L.; Das, B. C. Tetrahedron Lett. 1988, 29, 4423-4426
38. Marazano, C.; Yannic, S.; Genisson, Y.; Mehmandoust, M.; Das, B. C. Tetrahedron Lett. 1990, 31, 1995-1998
39. Matsumura, Y.; Nakamura, Y.; Maki, T.; Onomura, O. Tetrahedron Lett. 2000, 41, 7685-7689 For diastereoselective Diels-Alder reactions of chiral acrylic acid derivatives with dihydropyridines, see: Kouklovsky, C.; Pouilhès, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672-6679
40. Campbell, M. M.; Sainsbury, M.; Searle, P. A.; Davies, G. M. Tetrahedron Lett. 1992, 33, 3181-3184
41. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243-4244
42. Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79-87
43. See Supporting Information for more details.
44. Using our optimized conditions from Table 1, 100% conversion of the homoallylic alcohol to its corresponding terminal alkene dimers was observed.
45. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 6, 953-956
46. Salaun, J.; Karkour, B.; Ollivier, J. Tetrahedron 1989, 45, 3151-3162
47. Maxey, K. M.; Bundy, G. L. Tetrahedron Lett. 1980, 21, 445-448
48. Tsuji, J. Synthesis 1984, 369-384
49. Unpublished results.
50. For the asymmetric total synthesis of lyconadin A, see: Reference 7.
51. Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 418-419 For lyconadin A and B, see: Beshore, D. C.; Smith, A. B., III. J. Am. Chem. Soc. 2007, 129, 4148-4149
52. Beshore, D. C.; Smith, A. B., III. J. Am. Chem. Soc. 2008, 130, 13778-13789