Stereoselective syntheses of functionalized spirocyclopenteneoxindoles via triphenylphosphine-catalyzed [3+2] cycloaddition reactions

Molecular Diversity

Volumn 17, Issue 3, 2013, Pages 563-571

  Zhou, Qing Fa ^a   Chu, Xue Ping ^a   Ge, Fei Fei ^a   Li, Cheng ^a   Lu, Tao ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

3+2 Cycloaddition reaction; Alkylidene oxindole; Spirocyclopenteneoxindole; Triphenylphosphine; Ynone

Indexed keywords

ACETONITRILE; INDOLE DERIVATIVE; OXINDOLE; SPIROCYCLOPENTENEOXINDOLE DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; ELECTRON TRANSPORT; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; CYCLOADDITION REACTION; CYCLOPENTANES; DRUG DESIGN; INDOLES; ORGANOPHOSPHORUS COMPOUNDS; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84880774243     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-013-9456-8     Document Type: Article

References (57)

1. Magnus P, Mugrage B, Deluca MR, Cain GA (1990) Studies on gelsemium alkaloids. Total synthesis of (+)-koumine, (+)-taberpsychine, and (+)-koumidine. J Am Chem Soc 112:5220-5230. doi: 10.1021/ja00169a033
2. Galliford CV, Scheidt K (2007) Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents. Angew Chem Int Ed 46:8748-8758. doi: 10.1002/anie.200701342
3. Wearing XZ, Cook JM (2002) Enantiospecific, stereospecific total synthesis of the oxindole alkaloid alstonisine. Org Lett 4:4237-4240. doi: 10.1021/ol020170b
4. Yang J, Wearing XZ, Le Quesne PW, Deschamps JR, Cook JMJ (2008) Enantiospecific synthesis of (+)-alstonisine via a stereospecific osmylation process. Nat Prod 71:1431-1440. doi: 10.1021/np800269k
5. Canner JA, Sobo M, Ball S, Hutzen B, DeAngelis S, Willis W, Studebaker AW, Ding K, Wang S, Yang D, Lin J (2009) MI-63: a novel small-molecule inhibitor targets MDM2 and induces apoptosis in embryonal and alveolar rhabdomyosarcoma cells with wild-type p53. Br J Cancer 101:774-781. doi: 10.1038/sj.bjc.6605199
6. Marti C, Carreira EM (2003) Construction of spiro[pyrrolidine-3,3′' -oxindoles]-recent applications to the synthesis of oxindole alkaloids. Eur J Org Chem 2003:2209-2219. doi: 10.1002/ejoc.200300050
7. WilliamsRM Cox R (2003) Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report. Acc Chem Res 36:127-139. doi: 10.1021/ar020229e
8. Fensome A, Koko M, Wrobel J, Zhang P, Zhang Z, Cohen J, Lundeen S, Rudnick K, Zhu Y, Winneker R (2003) Novel 5-aryl-1,3-dihydro-indole-2-thiones: potent, orally active progesterone receptor agonists. Bioorg Med Chem Lett 13:1317-1320. doi: 10.1016/S0960-894X(03)00129-X
9. Beccalli EM, Clerici F, Gelmi ML (2003) A new synthetic procedure to spiro[cyclohexane-1,3′' -indoline]-2′',4-diones. Tetrahedron 59:4615-4622. doi: 10.1016/S0040-4020(03)00627-6
10. Antonchick AP, Gerding-Reimers C, Catarinella M, Schuermann M, Preut H, Ziegler S, Rauh D, Waldmann H (2010) Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products. Nat Chem 2:735-740. doi: 10.1038/nchem.730
11. Kotha S, Deb AC, Lahiri K, Manivannan E (2009) Selected synthetic strategies to spirocyclics. Synthesis 2009:165-193. doi: 10.1055/s-0028-1083300
12. Greshock TJ, Grubbs AW, Jiao P, Wicklow DT, Gloer JB, Williams RM (2008) Isolation, structure elucidation, and biomimetic total synthesis of versicolamideB, and the isolation of antipodal (-)-stephacidinA and (+)-notoamideB from Aspergillus versicolor NRRL35600. Angew Chem Int Ed 47:3573-3577. doi: 10.1002/anie.200800106
13. Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wu TY, He Y (2006) Design, synthesis and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 16:2105-2108. doi: 10.1016/j.bmcl.2006.01.073
14. Serradeil-Le Gal C, Lacour C, Valette G, Garcia G, Foulon L, Galindo G, Bankir L, Pouzet B, Guillon G, Barberis C, Chicot D, Jard S, Vilain P, Garcia C, Marty E, Raufaste D, Brossard G, Nisato D, Maffrand JP, Le Fur G (1996) Characterization of SR 121463A, a highly potent and selective, orally active vasopressin V2 receptor antagonist. J Clin Investig 98:2729-2738. doi: 10.1172/JCI119098
15. Ding Q, Liu JJ, Zhang Z (2007) WO 2007/104714
16. Hershenson FM, Prodan KA, Kochman RL, Bloss JL, Mackerer CR (1977) Synthesis of beta-spiro[pyrrolidinoindolines], their binding to the glycine receptor, and in vivo biological activity. J Med Chem 20:1448-1451. doi: 10.1021/jm00221a016
17. Makings LR, Garcia-Guzman Blanco M, Hurley DJ, Drutu I, Raffai G, Bergeron DM, Nakatani A, Termin AP, Silina A (2007) WO 2007100670
18. 1 antagonists 2: a pharmacophore model for arylsulfonamide binding. Bioorg Med Chem Lett 8:1851-1856
19. Palucki BL, Feighner SD, Pong SS, McKee KK, Hrenuik DL, Tan C, Howard AD, Van der Ploeg LHY, Patchett AA, Nargund RP (2001) Spiro(indoline-3,4′- piperidine) growth hormone secretagogues as ghrelin mimetics. Bioorg Med Chem Lett 11: 1955-1957
20. Trost BM, Brennan MK (2009) Asymmetric syntheses of oxindole and indole spirocyclic alkaloid natural products. Synthesis 2009:3003-3025. doi: 10.1055/s-0029-1216975
21. Trost BM, Jiang C (2006) Catalytic enantioselective construction of all-carbon quaternary stereocenters. Synthesis 2006:369-396. doi: 10.1055/s-2006-926302
22. Marti C, Carreira EM (2003) Construction of Spiro[pyrrolidine-3,3′' -oxindoles]-recent applications to the synthesis of oxindole alkaloids. Eur J Org Chem 2003:2209-2219. doi: 10.1002/ejoc.200300050
23. Ball-Jones NR, Badillo JJ, Franz AK (2012) Strategies for the enantioselective synthesis of spirooxindoles. Org Biomol Chem 10:5165-5181. doi: 10.1039/C2OB25184A
24. Finch N, Hsu IHC, Gemenden CW, Taylor WI (1963) Oxidative transformations of indole alkaloids. II. The preparation of oxindoles from cis-DE-Yohimbinoid alkaloids. The partial synthesis of carapanaubine. J Am Chem Soc 85:1520-1523. doi: 10.1021/ja00893a029
25. Palmisano G, Annunziata R, Papeo G, Sisti M (1996) Oxindole alkaloids. A novel non-biomimetic entry to (-)-Horsfiline. Tetrahedron: Asymmetry 7: 1-4
26. Carpenter NE, Kucera DJ, Overman LE (1989) Palladium-catalyzed polyene cyclizations of trienyl triflates. J Org Chem 54:5846-5848. doi: 10.1021/jo00286a009
27. Von Nussbaum F, Danishefsky SJ (2000) A rapid total synthesis of spirotryprostatinB: proof of its relative and absolute stereochemistry. Angew Chem Int Ed 39:2259-2262. doi: 10.1002/1521-3757(20000616)
28. Kuzmich D, Wu SC, Ha DC, Lee CS, Ramesh S, Atarashi S, Choi JK, Hart DJ (1994) Total synthesis of dl-21-oxogelsemine. J Am Chem Soc 116:6943-6944. doi: 10.1021/ja00094a062
29. Jiang K, Jia ZJ, Yin X, Wu L, Chen YC (2010) Asymmetric quadruple aminocatalytic domino reactions to fused carbocycles incorporating a spirooxindole motif. Org Lett 12:2766-2769. doi: 10.1021/ol100857s
30. Wei Q, Gong LZ (2010) Organocatalytic asymmetric formal [4+2] cycloaddition for the synthesis of spiro[4-cyclohexanone-1,3′' -oxindoline] derivatives in high optical purity. Org Lett 12:1008-1011. doi: 10.1021/ol100020v
31. Wu B, Chen J, Li M, Zhang JX, Xu XP, Ji SJ, Wang XW (2012) Highly enantioselective synthesis of spiro[cyclohexanone-oxindoles] and spiro[cyclohexanone-pyrazolones] by asymmetric cascade [5+1] double Michael reactions. Eur J Org Chem 2012:1318-1327. doi: 10.1002/ejoc.201101529
32. Wei XP, Chen CX, Lu RJ, Wang JJ, Zhang XJ, Yan M (2012) Enantioselective synthesis of 3,3′' -dihydropyrryl-spirooxindoles via an organocatalytic three-component reaction. Org Biomol Chem 10:5245-5252. doi: 10.1039/C2OB25629K
33. Wenkert E, Liu S (1992) Intramolecular reactions of oxindolyl diazo ketones. Synthesis 1992:323-327. doi: 10.1055/s-1992-26101
34. Pettersson M, Knueppel D, Martin SF (2007) Concise, stereoselective approach to the spirooxindole ring system of citrinadin A. Org Lett 9:4623-4626. doi: 10.1021/ol702132v
35. Richmond E, Duguet N, Slawin AMZ, Lebl S, Smith A (2012) Asymmetric pericyclic cascade approach to spirocyclic oxindoles. Org Lett 14:2762-2765. doi: 10.1021/ol300982f
36. Lu X, Zhang C, Xu Z (2001) Reactions of electron-deficient alkynes and allenes under phosphine catalysis. Acc Chem Res 34:535-544. doi: 10.1021/ar000253x
37. Methot JL, Roush WR (2004) Nucleophilic phosphine organocatalysis. Adv Synth Catal 346:1035-1050. doi: 10.1002/adsc.200404087
38. Nair V, Menon RS, Sreekanth AR, Abhilash N, Biju AT (2006) Engaging zwitterions in carbon-carbon and carbon-nitrogen bond-forming reactions: a promising synthetic strategy. Acc Chem Res 39:520-530. doi: 10.1021/ar0502026
39. Ye LW, Zhou J, Tang Y (2008) Phosphine-triggered synthesis of functionalized cyclic compounds. Chem Soc Rev 37:1140-1152. doi: 10.1039/B717758E
40. Marinetti A, Voituriez A (2010) Enantioselective phosphine organocatalysis. Synlett 2010:174-194. doi: 10.1055/s-0029-1219157
41. Cowen BJ, Miller SJ (2009) Enantioselective catalysis and complexity generation from allenoates. Chem Soc Rev 38:3102-3116. doi: 10.1039/B816700C
42. Xu Z, Lu X (1997) Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and NN -tosylimines. A novel approach to nitrogen heterocycles. Tetrahedron Lett 38:3461- 3464
43. Zhu X, Lan J, Kwon O (2003) An expedient phosphine-catalyzed [4+2] annulation: synthesis of highly functionalized tetrahydropyridines. J Am Chem Soc 125:4716-4717. doi: 10.1021/ja0344009
44. Wang JC, Krische MJ (2003) Intramolecular organocatalytic [3+2] dipolar cycloaddition: stereospecific cycloaddition and the total synthesis of (pm) ±) -hirsutene. Angew Chem Int Ed 115:6035-6037. doi: 10.1002/ange. 200352218
45. Henry CE, Kwon O (2007) Phosphine-catalyzed synthesis of highly functionalized coumarins. Org Lett 9:3069-3072. doi: 10.1021/ol071181d
46. Tejedor D, Santos-Exposito A, Mendez-Abt G, Ruiz-Perez C, Garcia-Tellado F (2009) Trialkylamine versus trialkylphosphine: catalytic conjugate addition of alcohols to alkyl propiolates. Synlett 2009:1223-1226. doi: 10.1055/s-0028-1216727
47. Yavari I, Souri S, Sirouspour M, Djahaniani H (2006) Vinylphosphonium salt mediated reaction between alkyl propiolates and aminophenols or hydroxyphenols. Synthesis 2006:3243-3249. doi: 10.1055/s-2006-950230
48. Guan XY, Wei Y, Shi M (2010) Phosphine-catalyzed tandem reaction of allenoates with nitroalkenes. Org Lett 12:5024-5027. doi: 10.1021/ol102191p
49. Hu J, Wei Y, Tong X (2011) Phosphine-catalyzed [3+2] annulations ofγ γ -functionalized butynoates and 1C,3O-bisnucleophiles: highly selective reagent-controlled pathways to polysubstituted furans. Org Lett 13:3068-3071. doi: 10.1021/ol200940a
50. 33 -catalyzed unexpected α -addition reaction of 1-(o -hydroxyaryl)-1,3-diketones to terminal alkynoates: a straightforward synthesis of multifunctional vinylesters. Chem Commun 2009:6089-6091. doi: 10.1039/B909279J
51. Zhang XC, Cao SH, Wei Y, Shi M (2011) Phosphine-catalyzed highly diastereoselective [3+2] cyclization of isatin derived electron-deficient alkenes with α -allenic esters. Chem Commun 47:1548-1550. doi: 10.1039/C0CC04289G
52. Kuroda H, Tomita I, Endo T (2003) Novel phosphine-catalyzed zipper cyclization of aliphatic diyne-dione and yne-dione systems. Org Lett 5:129-131. doi: 10.1021/ol020198n
53. Wilson JE, Sun J, Fu GC (2010) Stereoselective phosphine-catalyzed synthesis of highly functionalized diquinanes. Angew Chem Int Ed 49:161-163. doi: 10.1002/anie.200905125
54. Lian Z, Shi M (2012) Nitrogen- and phosphorus-containing Lewis base catalyzed [4+2] and [3+2] annulation reactions of isatins with but-3-yn-2-one. Eur J Org Chem 2012:581-586. doi: 10.1002/ejoc.201101338
55. Yang L, Xie P, Li E, Li X, Huang Y, Chen R (2012) Phosphine-catalyzed domino reaction: an efficient method for the synthesis of highly functionalized spirooxazolines. Org Biomol Chem 10:7628-7634. doi: 10.1039/C2OB26338F
56. Yong SR, Williams MC, Pyne SG, Ung AT, Skelton BW, White AH, Turner P (2005) Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions. Tetrahedron 61:8120-8129. doi: 10.1016/j.tet.2005.06.050
57. Trost BM, Dake GR (1997) Nucleophilic alpha-addition to alkynoates. A synthesis of dehydroamino acids. J Am Chem Soc 119:7595-7596. doi: 10.1021/ja971238z