Ammonia synthons for the multicomponent assembly of complex γ-lactams

Proceedings of the National Academy of Sciences of the United States of America

Volumn 108, Issue 17, 2011, Pages 6781-6786

  Tan, Darlene Q ^a   Martin, Kevin S ^a   Fettinger, James C ^a   Shaw, Jared T ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Multicomponent reaction; Stereoselective

Indexed keywords

AMMONIA; GAMMA LACTAM DERIVATIVE; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS; SYNTHON; X RAY CRYSTALLOGRAPHY;

AMMONIA; CRYSTALLOGRAPHY, X-RAY; LACTAMS; MOLECULAR STRUCTURE;

EID: 79955570370     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1015261108     Document Type: Article

References (47)

1. Guntern A, et al. (2003) Heliotropamide, a novel oxopyrrolidine-3- carboxamide from Heliotropium ovalifolium. J Nat Prod 66:1550-1553. (Pubitemid 38036704)
2. Younai A, Chin GF, Fettinger JC, Shaw JT (2010) Diastereoselective synthesis of (±)- heliotropamide by a one-pot, four-component reaction. J Org Chem 75:8333-8337.
3. Okazaki Y, Ishihara A, Nishioka T, Iwamura H (2004) Identification of a dehydrodimer of avenanthramide phytoalexin in oats. Tetrahedron 60:4765-4771. (Pubitemid 38595497)
4. Okazaki Y, Ishizuka A, Ishihara A, Nishioka T, Iwamura H (2007) New dimeric compounds of avenanthramide phytoalexin in oats. J Org Chem 72:3830-3839. (Pubitemid 46762470)
5. Omura S, et al. (1991) Structure of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells. J Antibiot 44:117-118.
6. Feling RH, et al. (2003) Salinosporamide A: A highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora. Angew Chem Int Edit 42:355-357. (Pubitemid 36176323)
7. Lettan RB, Galliford CV, Woodward CC, Scheidt KA (2009) Amide enolate additions to acylsilanes: In situ generation of unusual and stereoselective homoenolate equivalents. J Am Chem Soc 131:8805-8814.
8. Raup DEA, Cardinal-David B, Holte D, Scheidt KA (2010) Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactams. Nat Chem 2:766-771.
9. Tang Y, Fettinger JC, Shaw JT (2009) One-step synthesis of complex nitrogen heterocycles from imines and alkyl-substituted maleic anhydrides. Org Lett 11:3802-3805.
10. Zhu J, Bienaymé H, eds. (2005) Multicomponent Reactions (Wiley-VCH Verlag, Weinheim, Germany) p 468.
11. Simon C, Constantieux T, Rodriguez J (2004) Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions. Eur J Org Chem 2004:4957-4980. (Pubitemid 40039228)
12. Kappe CO, Stadler A (2004) The Biginelli dihydropyrimidine synthesis. Org Reactions 63:1-116.
13. Doemling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17-89.
14. Biggs-Houck JE, Younai A, Shaw JT (2010) Recent advances in multicomponent reactions for diversity-oriented synthesis. Curr Opin Chem Biol 14:371-382.
15. Wei J, Shaw JT (2007) Diastereoselective synthesis of γ-lactams by a one-pot, four-component reaction. Org Lett 9:4077-4080.
16. Burdack C, Kalinski C, Ross G, Weber L, Khazak V ( 25, 2010) European Patent Office EPO 2009-EP6670 2010028862.
17. Kazmaier U, Hebach C (2003) Peptide syntheses via Ugi reactions with ammonia. Synlett 1591-1594. (Pubitemid 37100426)
18. Thompson MJ, Chen B (2009) Ugi reactions with ammonia offer rapid access to a wide range of 5-aminothiazole and oxazole derivatives. J Org Chem 74:7084-7093.
19. Wuts PGM, Greene TW (2007) Greene's Protective Groups in Organic Synthesis (John Wiley & Sons, Inc., Hoboken, NJ), 4th Ed, p 1082.
20. Carlier PR, Zhao H, MacQuarrie-Hunter SL, DeGuzman JC, Hsu DC (2006) Enantioselective synthesis of diversely substituted quaternary 1,4-benzodiazepin-2-ones and 1, 4-benzodiazepine-2,5-diones. J Am Chem Soc 128:15215-15220. (Pubitemid 44853532)
21. Fernandez R, et al. (2004) A practical oxidative method for the cleavage of hydrazide N-N bonds. Chem Eur J 10:737-745.
22. Lebrun S, Couture A, Deniau E, Grandclaudon P (2009) A practical photochemically induced method for N-N bond cleavage of N,N-disubstituted hydrazides. Synlett 2621-2624.
23. Plante OJ, Buchwald SL, Seeberger PH (2000) Halobenzyl ethers as protecting groups for organic synthesis. J Am Chem Soc 122:7148-7149. (Pubitemid 30639904)
24. Effenberger F, Mueller W, Keller R, Wild W, Ziegler T (1990) Amino acids. 8. A novel synthesis of γ-carboxy-L-glutamic acid from L-5-oxoproline esters. J Org Chem 55:3064-3067. (Pubitemid 20197842)
25. Ito Y, Kobayashi Y, Kawabata T, Takase M, Terashima S (1989) Novel syntheses of the carbapenem key intermediates, (3R,4R)-4-acetoxy-3-[(R)-1-(tert- butyldimethylsilyloxy) ethyl]-2-azetidinone and (3S,4R)-3-[(R)-1-(tert- butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-ethyl lactate. Tetrahedron 45:5767-5790. (Pubitemid 19234115)
26. Kanno O, Miyauchi M, Kawamoto I (2000) Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone derivatives. Heterocycles 53:173-181.
27. Wee AGH, McLeod DD (2000) Studies on the Rh(II)-catalyzed C-H insertion reaction of some derivatives of N-{4-[(S)-1,2-dihydroxybutyl]} alpha -diazo anilides: Site-selectivity. Heterocycles 53:637-655.
28. Dai C-F, Cheng F, Xu H-C, Ruan Y-P, Huang P-Q (2007) Diversity-oriented asymmetric synthesis of hapalosin: Construction of three small C9/C4/C3-modified hapalosin analogue libraries. J Comb Chem 9:386-394.
29. Huang P-Q, Guo Z-Q, Ruan Y-P (2006) A versatile approach for the asymmetric syntheses of (1R,9aR)-epiquinamide and (1R,9aR)-homopumiliotoxin 223G. Org Lett 8:1435-1438. (Pubitemid 43587457)
30. Meng W-H, Wu T-J, Zhang H-K, Huang P-Q (2004) Asymmetric syntheses of protected (2S,3S,4S)-3-hydroxy-4-methylproline and 4′-tert-butoxyamido- 2′-deoxythymidine. Tetrahedron Asymmetry 15:3899-3910. (Pubitemid 39593476)
31. Liu G, et al. (2008) Design, synthesis, and biological evaluation of caprolactam-modified bengamide analogues. ChemMedChem 3:74-78.
32. Maes BUW, Loones KTJ, Hostyn S, Diels G, Rombouts G (2004) Rapid palladium-catalyzed aminations of aryl chlorides with aliphatic amines under temperature-controlled microwave heating. Tetrahedron 60:11559-11564. (Pubitemid 39505322)
33. Borthwick AD, et al. (2002) Design and synthesis of pyrrolidine-5,5- trans-lactams (5-oxohexahydropyrrolo[3,2-b]pyrroles) as novel mechanism-based inhibitors of human cytomegalovirus protease. 2. Potency and chirality. J Med Chem 45:1-18. (Pubitemid 34038539)
34. Gage JR, Evans DA (1990) Diastereoselective aldol condensation using a chiral oxazolidinone auxiliary. Org Synth 68:83-91.
35. Sibi MP, Gorikunti U, LiuM(2002) Temperature dependent reversal of stereochemistry in enantioselective conjugate amine additions. Tetrahedron 58:8357-8363. (Pubitemid 35279736)
36. Dieltiens N, et al. (2006) The pyroglutamate hydantoin rearrangement. Eur J Org Chem 2006:2649-2660.
37. Occhiato EG, Prandi C, Ferrali A, Guarna A (2005) Remote stereocontrol in the Nazarov reaction: A new approach to the core of roseophilin. J Org Chem 70:4542-4545. (Pubitemid 40734177)
38. Ghinet A, et al. (2010) Studies on pyrrolidinones. On the application of copper-catalyzed arylation of methyl pyroglutamate to obtain a new benzo[de]quinoline scaffold. Tetrahedron 66:215-221.
39. Phillips DP, et al. (2009) Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride. Tetrahedron Lett 50:7293-7296.
40. Yamada K, Kubo T, Tokuyama H, Fukuyama T (2002) A mild copper-mediated intramolecular amination of aryl halides. Synlett 231-234. (Pubitemid 34132711)
41. Yin J, Buchwald SL (2000) Palladium-catalyzed intermolecular coupling of aryl halides and amides. Org Lett 2:1101-1104.
42. Chan DMT, Monaco KL, Wang R-P, Winters MP (1998) New N- and O-arylation with phenylboronic acids and cupric acetate. Tetrahedron Lett 39:2933-2936. (Pubitemid 28184063)
43. Evans DA, Katz JL, West TR (1998) Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine. Tetrahedron Lett 39:2937-2940. (Pubitemid 28184064)
44. Abe T, Takeda H, Yamada K, Ishikura M (2008) Copper-catalyzed N-arylation reaction of 2-azabicyclo[2.2.1]hept-5-en-3-one with arylboronic acids under microwave irradiation. Heterocycles 76:133-136.
45. Bolshan Y, Batey RA (2008) Enamide synthesis by copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts. Angew Chem Int Ed 47:2109-2112.
46. Wang Q, Schreiber SL (2009) Copper-mediated amidation of heterocyclic and aromatic C-H bonds. Org Lett 11:5178-5180.
47. Borthwick AD, et al. (2003) Design and synthesis of pyrrolidine-5, 5′-trans-lactams (5-oxo-hexahydropyrrolo[3,2-b]pyrroles) as novel mechanism-based inhibitors of human cytomegalovirus protease. 4. Antiviral activity and plasma stability. J Med Chem 46:4428-4449. (Pubitemid 37238746)