Formal enantioselective total synthesis of schulzeines A-C via Pd-catalyzed intramolecular asymmetric allylic amination

Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 6240-6249

  Lin, Chi Feng ^a   Ojima, Iwao ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ALLYLIC AMINATION; ENANTIOPURE; ENANTIOSELECTIVE TOTAL SYNTHESIS; RING-CLOSING METATHESIS REACTIONS;

AMINES; CHELATION; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

CATALYSIS;

DIPHOSPHONITE LIGAND; LIGAND; PALLADIUM; RUTHENIUM; UNCLASSIFIED DRUG;

ALLYLIC REARRANGEMENT; AMINATION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; IODINATION; RING CLOSING METATHESIS; SYNTHESIS;

ALLYL COMPOUNDS; AMINATION; CATALYSIS; HETEROCYCLIC COMPOUNDS, 3-RING; LACTAMS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; QUINOLIZIDINES; STEREOISOMERISM; SULFURIC ACID ESTERS;

EID: 79961073742     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2009615     Document Type: Article

References (26)

1. Takada, K.; Uehara, T.; Nakao, Y.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Am. Chem. Soc. 2004, 126, 187
2. Braun, C.; Brayer, G. D.; Withers, S. G. J. Biol. Chem. 1995, 270, 26778
3. Dwek, R. A.; Butters, T. D.; Platt, F. M.; Zitzmann, N. Nat. Rev. Drug Discovery 2002, 1, 65
4. Mehta, A.; Zitzmann, N.; Rudd, P. M.; Block, T. M.; Dwek, R. A. FEBS Lett. 1998, 430, 17
5. Kuntiyong, P.; Akkarasamiyo, S.; Eksintkun, G. Chem. Lett. 2006, 35, 1008
6. Gurjar, M. K.; Pramanik, C.; Bhattasali, D.; Ramana, C. V.; Mohapatra, D. K. J. Org. Chem. 2007, 72, 6591
7. Liu, G.; Romo, D. Org. Lett. 2009, 11, 1143
8. Bowen, E. G.; Wardrop, D. J. J. Am. Chem. Soc. 2009, 131, 6062
9. Miyazaki, M.; Ando, N.; Sugai, K.; Seito, Y.; Fukuoka, H.; Kanemitsu, T.; Nagata, K.; Odanaka, Y.; Nakamura, K. T.; Itoh, T. J. Org. Chem. 2011, 76, 534
10. Vicario, J. L.; Badía, D.; Carrillo, L.; Etxebarria, J. Curr. Org. Chem. 2003, 7, 1775
11. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341
12. Kaufman, T. S. Synthesis 2005, 339
13. Ito, K.; Akashi, S.; Saito, B.; Katsuki, T. Synlett 2003, 1809
14. Taylor, A. M.; Schreiber, S. L. Org. Lett. 2006, 8, 143
15. Teichert, J. F.; Fañanás-Mastral, M.; Feringa, B. L. Angew. Chem., Int. Ed. 2011, 50, 688
16. For the use of RCM for the third ring from 1-vinyltetrahydroisoquinoline using achiral ω-alkenylamide tethers, see Kinderman, S. S.; Wekking, M. M. T.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2005, 70, 5519
17. Denmark, S. E.; Regens, C. S.; Kobayashi, T. J. Am. Chem. Soc. 2007, 129, 2774
18. Shi, C.; Ojima, I. Tetrahedron 2007, 63, 8563
19. Shi, C. Ph.D. Thesis, Development and Applications of Chiral Phosphorus Ligands Transition-Metal Catalyzed Asymmetric Reactions. Stony Brook University, Stony Brook, NY, 2008.
20. Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. 1995, 34, 2386
21. Shi, C.; Chien, C.-W.; Ojima, I. Chem. Asian J. 2011, 6, 674
22. Organ, M. G.; Xu, J.; N'Zemba, B. Tetrahedron Lett. 2002, 43, 8177
23. Rajendra, G.; Miller, M. J. J. Org. Chem. 1987, 52, 4471
24. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953
25. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168
26. Thakkar, K.; Geahlen, R. L.; Cushman, M. J. Med. Chem. 1993, 36, 2950