Chemistry of the hexahydropyrrolo[2,3-b]indoles: Configuration, conformation, reactivity, and applications in synthesis

Accounts of Chemical Research

Volumn 40, Issue 2, 2007, Pages 151-161

  Crich, David ^a   Banerjee, Abhisek ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BENZOFURAN DERIVATIVE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; HEXAHYDROINDOLINONE; INDOLE ALKALOID; INDOLE DERIVATIVE; OCTANE; TRYPTAMINE; TRYPTAMINE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

AMINO ACIDS; BENZOFURANS; BICYCLO COMPOUNDS, HETEROCYCLIC; INDOLE ALKALOIDS; INDOLES; KINETICS; OCTANES; STEREOISOMERISM; THERMODYNAMICS; TRYPTAMINES; TRYPTOPHAN;

EID: 33947408403     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050175j     Document Type: Article

References (74)

1. Hino, T.; Nakagawa, M. Chemistry and Reactions of Cyclic Tautomers of Tryptamines and Tryptophans. Alkaloids 1988, 34, 1-75.
2. Anthoni, U.; Christophersen, C; Nielsen, P. H. Naturally Occurring Cyclotryptophans and Cyclotryptamines. Alkaloids 1999, 13, 163-236.
3. Julian, P. L.; Pikl, J. Studies in the Indole Series. V. The Complete Synthesis of Physostigmine (Eserine). J. Am. Chem. Soc. 1935, 57, 755-757.
4. King, F. E.; Robinson, R. Synthesis of Physostigmine. VI. Synthesis of dl-Esermethole Methopicrate. J. Chem. Soc. 1932, 1433-1438.
5. Takano, S.; Ogasawara, K. Alkaloids of the Calabar Bean. Alkaloids 1989, 36, 225-251.
6. Trost, B. M.; Zhang, Y. Molybdenum-Catalyzed Asymmetric Allylation of 3-Alkyloxindoles: Application to the Formal Total Synthesis of (-)-Physostigmine. J. Am. Chem. Soc. 2006, 128, 4590-4591.
7. Lebsack, A. D.; Link, J. T.; Overman, L. E.; Stearns, B. A. Enantioselective Total Synthesis of Quadrigemine C and Psycholeine. J. Am. Chem. Soc. 2002, 124, 9008-9009.
8. Kamenecka, T. M.; Danishefsky, S. J. Discovery Through Total Synthesis: A Retrospective on the Himastatin Problem. Chem. Eur. J. 2001, 7, 41-63.
9. Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. Total Synthsis of 5-N-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents. J. Am. Chem. Soc. 1999, 121, 11953-11963.
10. Schkeryantz, J. M.; Woo, J. C. G.; Siliphaivanh, P.; Depew, K. M.; Danishefsky, S. J. Total Synthesis of Gypsetin, Deoxybrevianamide E, Brevianamide E, and Tryprostatin B: Novel Constructions of 2,3-Disubstituted Indoles. J. Am. Chem. Soc. 1999, 121, 11964-11975.
11. Cox, R. J.; Williams, R. M. The Paraherquamides, Brevianamides and Asperparaline: Laboratory Synthesis and Biosynthesis. An Interim Report. Acc. Chem. Res. 2003, 36, 127-139.
12. Richard, D. J.; Schiavi, B.; Joullie, M. M. Synthetic Studies of Roquefortine C: Synthesis of Isoroquefortine C and a Heterocycles. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11971-11976.
13. Hewitt, P. R.; Cleator, E.; Ley, S. V. A Concise Total Synthesis of (+)-Okaramine C. Org. Biomol. Chem. 2004, 2, 2415-2417.
14. Didier, C; Critcher, D. J.; Walshe, N. D.; Kojima, Y.; Yamanuchi, Y.; Barrett, A. G. M. Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662. J. Org. Chem. 2004, 69, 7875-7879.
15. Taniguchi, M.; Hino, T. Cyclic Tautomers of Tryptophans and Tryptamines. 4. Synthesis of Cyclic Tautomers of Tryptophans and Tryptamines. Tetrahedron 1981, 37, 1487-1494.
16. Crich, D.; Davies, J. W. Asymmetric Synthesis of α-Alkylated Tryptophan Derivatives. J. Chem. Soc., Chem. Commun. 1989, 1418-1419.
17. Bourne, G. T.; Crich, D.; Davies, J. W.; Horwell, D. C. Enantiospecific Synthesis with Amino Acids. Part 1. Tryptophan as a Chiron for the Synthesis of α-Substituted Tryptophan Derivatives. J. Chem. Soc., Perkin Trans. 1 1991, 1693-1699.
18. Chan, C. 0.; Crich, D.; Natarajan, S. Enantiospecific Synthesis of Amino Acids: Preparation of (R)- and (S)-α-Methylaspartic Acid from (S)-Tryptophan. Tetrahedron Lett. 1992, 33, 3405-3408.
19. Crich, D.; Lim, L. B. L. Asymmetric Synthesis of α-Substituted 5-Hydroxytryptophan Derivatives. Heterocycles 1993, 36, 1199-1204.
20. Crich, D.; Bruncko, M.; Natarajan, S.; Teo, B. K.; Tocher, D. A. Conformational Analysis of Substituted Hexahydropyrrolo[2,3-b] indoles and Related Systems. An Unusual Example of Hindered Rotation about Sulfonamide S-N Bonds. An X-Ray Crystallographic and NMR Study. Tetrahedron 1995, 51, 2215-2228.
21. Crich, D.; Chan, C. O.; Davies, J. W.; Natarajan, S.; Vinter, J. G. Enantiospecific Synthesis with Amino Acids. Part 2. α-Alkylation of Tryptophan: A Chemical and Computational Investigation of Cyclic Tryptophan Tautomers. J. Chem. Soc., Perkin Trans. 2 1992, 2233-2240.
22. Somei, M.; Kawasaki, T.; Fukui, Y.; Yamada, F.; Kobayashi, T.; Aoyama, H.; Shinmoy, D. The Chemistry of 1-Hydroxyindole Derivatives: Nucleophilic Substitution Reaction on Indole Nucleus. Heterocycles 1992, 34, 1877-1884.
23. Benedetti, E.; Ciajolo, M. R.; Maisto, A. Crystal Structure of N-(tert-Butyloxycarbonyl)-L-Proline. Acta Crystallogr., Sect. B 1974, 30, 1783-1788.
24. 1,3 Strain). Helv. Chim. Acta 1992, 75, 913-934.
25. Pauling, P.; Petcher, T. J. Crystal and Molecular Structure of Eserine (Physostigmine). J. Chem. Soc., Perkin Trans. 2 1973, 1342-1345.
26. Civitello, E. R.; Rapoport, H. Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2. J. Org. Chem. 1994, 59, 3775-3782.
27. Iyer, R. S.; Coles, B. F.; Raney, K. D.; Thier, R.; Guengerich, F. P.; Harris, T. M. DNA Adduction by the Potent Carcinogen Aflatoxin B1: Mechanistic Studies. J. Am. Chem. Soc. 1994, 116, 1603-1609.
28. Graybill, T. L; Casillas, E. G.; Pal, K.; Townsend, C. A. Silyl Triflate-Mediated Ring-Closure and Rearrangement in the Synthesis of Potential Bisfuran-Containing Intermediates of Aflatoxin Biosynthesis. J. Am. Chem. Soc. 1999, 121, 7729-7746.
29. Bujons, J.; Sanchez-Baeza, F.; Messeguer, A. A Study of the Interconversion between 3,4-Dihydro-4-formyl-2-hydroxy-2H-benzopyran and 2,3,3a,8a-Tetrahydro-2-hydroxyfuro[2,3-b]benzofuran Moieties, and its Application to a Formal Synthesis of (+)-Aflatoxin B1. Tetrahedron 1994, 50, 7597-7610.
30. Morales-Rios, M. S.; Santos-Sanchez, N. F.; Suarez-Castillo, O. R.; Joseph-Nathan, P. Conformational Studies on Indole Alkaloids from Flustra foliacea by NMR and Molecular Modeling. Magn. Reson. Chem. 2002, 40, 677-682.
31. Morales-Rios, M. S.; Santos-Sanchez, N. F.; Perez-Rojas, N. A.; Joseph-Nathan, P. Conformational Insights into Furo- and Thieno-[2,3-b] indolines Derived from Coupling Constants and Molecular Modeling. Magn. Reson. Chem. 2004, 42, 973-976.
32. Kakiuchi, K.; Takeuchi, H.; Tobe, Y.; Odaira, Y. Synthesis of cis-Transoid-cis- and cis-Cisoid-cis-Tricyclo[6.3.0. 02,6]undecan-1-ols. Bull Chem. Soc. Jpn. 1985, 58, 1613-1614.
33. Ghera, E. Rearrangements of Five-Membered Rings of Restricted Mobility. J. Org. Chem. 1968, 33, 1042-1051.
34. Crich, D.; Huang, X. On the Reaction of Tryptophan Derivatives with N-Phenylselenyl Phthalimide: The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-b]indole Products. Alkylation of Tryptophan with Inversion of Configuration. J. Org. Chem. 1999, 64, 7218-7223.
35. Taniguchi, M.; Yamamoto, I.; Nakagawa, M.; Hino, T. Cyclic Tautomers of Tryptophans and Tryptamines. VIII. Cyclic Tautomers of Cyclo-L-Prolyl- L-Tryptophyl and Related Compounds. Chem. Pharm. Bull. 1985, 33, 4783-4791.
36. Caballero, E.; Avendano, C; Menendez, J. C. Stereochemical Issues Related to the Synthesis and Reactivity of Pyrazino[2′,1′-5,1]pyrrolo[2,3- b]indole-1,4-diones. Tetrahedron: Asymmetry 1998, 9, 967-981.
37. Seebach, D.; Sting, A. R.; Hoffmann, M. Self-Regeneration of Stereocenters (SRS) - Applications, Limitations, and Abandonment of a Synthetic Principle. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708-2748.
38. Schoellkopf, U.; Lonsky, R.; Lehr, P. Asymmetric Synthesis via Heterocyclic Intermediates, XXIV. Enantioselective Synthesis of (R)-α-Methyltryptophan Methyl Ester and D-Tryptophan Methyl Ester by the Bislactim Ether Route. Liebigs Ann. Chem. 1985, 413-417.
39. Gander-Coquoz, M.; Seebach, D. Synthesis of Enantiomerically Pure, α-Alkylated Lysine, Ornithine, and Tryptophan Derivatives. Helv. Chim. Acta 1988, 71, 224-236.
40. Crich, D.; Gress, I. P.; Quintero-Cortes, L.; Sandoral-Ramirez, J. The Chemistry of Cyclic Tautomers of Tryptophan: Highly Diastereoselective Aldol Condensations. Heterocycles 1994, 38, 719-724.
41. Zimmerman, S. C; Wu, W. A Rigid Molecular Tweezers with an Active Site Carboxylic Acid: Exceptionally Efficient Receptor for Adenine in an Organic Solvent. J. Am. Chem. Soc 1989, 111, 8054-8055.
42. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Stereoselective Alkylation at C(α) of Serine, Glyceric Acid, Threonine, and Tartaric acid Involving Heterocyclic Enolates with Exocyclic Double Bonds. Helv. Chim. Acta 1987, 70, 1194-1216.
43. Bruncko, M.; Crich, D. Cyclic Tautomers of Tryptophan: Enantio and Diastereoselective Synthesis of β-Substituted and α,β- Disubstituted Derivatives of Tryptophan. J. Org. Chem. 1994, 59, 4239-4249.
44. Bruncko, M.; Crich, D. Conformationally Restricted Amino Acids: Diastereoselective Substitution at the β-Position of L-Tryptophan. Tetrahedron Lett. 1992, 33, 6251-6254.
45. Kahne, D.; Walker, S.; Cheng, Y.; Van, Engen, D. Glycosylation of Unreactive Substrates. J. Am. Chem. Soc. 1989, 111, 6881-6882.
46. Lipshutz, B. H.; Sengupta, S. Organocopper Reagents: Substitution, Conjugate Addition, Carbo/Metallocupration, and Other Reactions. Org. React. 1992, 41, 135-631.
47. Hamada, T.; Nishida, A.; Yonemitsu, O. Selective Removal of Electron-Accepting p-Toluene- and Naphthalenesulfonyl Protecting Groups for Amino Function via Photoinduced Donor-Acceptor Ion Pairs with Electron-Donating Aromatics. J. Am. Chem. Soc. 1986, 108, 140-145.
48. Bruncko, M.; Crich, D.; Samy, R. Functionalization at C-3a of Tryptophan Derived Hexahydropyrrolo[2,3-b]indoles. Heterocycles 1993, 36, 1735-1738.
49. Bruncko, M.; Crich, D.; Samy, R. Chemistry of Cyclic Tautomers of Tryptophan: Formation of a Quaternary Center at C3a and Total Synthesis of the Marine Alkaloid (+)-ent-Debromoflustramine B. J. Org. Chem. 1994, 59, 5543-5549.
50. Crich, D.; Pavlovic, A. B.; Samy, R. The Chemistry of Cyclic Tautomers of Tryptophan: Total Synthesis of (+)-(ent)-Pseudophrynaminol. Tetrahedron 1995, 51, 6379-6384.
51. b-Methyl-4,5,6- tribromo-3-indoleacetamide. Chem. Pharm. Bull. 1990, 38, 2632-2636.
52. α- Alkyl-, 5-Chloro-, and 5-Nitrotryptophan Derivatives. Chem. Pharm. Bull. 1983, 31, 1856-1865.
53. Dua, R. K.; Phillips, R. S. Synthesis of 5-Cyano-L-Tryptophan. Tetrahedron Lett. 1992, 33, 29-32.
54. Walton, R.; Fraser-Reid, B. Studies on the Intramolecular Competitive Addition of Carbon Radicals to Aldehydo and Alkenyl Groups. J. Am. Chem. Soc. 1991, 113, 5791-5799.
55. b-Methyltryptamine. J. Am. Chem. Soc. 1975, 97, 6496-6501.
56. b- Methoxycar bonyltryptamine and Determination of Absolute Configuration of the Product. Synlett 1998, 257-258.
57. Yamada, F.; Fukui, Y.; Iwaki, T.; Ogasawara, S.; Okigawa, M.; Tanaka, S.; Somei, M. Synthesis of Optically Active Methyl 1,2,3,-3a,8,8a- Hexahydropyrrolo[2,3-b]indole-2-carboxylates having a Halogen or an Oxygen Functional Group at the 3a-Position. Heterocycles 2006, 67, 129-134.
58. Ley, S. V.; Cleator, E.; Hewitt, P. R. A Rapid Stereocontrolled Synthesis of the 3a-Hydroxypyrrolo[2,3-b]indole Skeleton, A Building Block for 10b-Hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]-indole-1, 4-diones. Org. Biomol. Chem. 2003, 1, 3492-3494.
59. Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. One Electron C-C Bond Forming Reactions via Allylstannanes: Scope and Limitations. Tetrahedron 1985, 41, 4079-4094.
60. Morales-Rios, M. S.; Suarez-Castillo, O. R.; Joseph-Nathan, P. General Approach to the Synthesis of Marine Bryozoan Flustra foliacea Alkaloids: Total Syntheses of Debromoflustramines A and B. J. Org. Chem. 1999, 64, 1086-1087.
61. Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition-Cyclization Strategy: Synthesis of (-)-Flustramine B. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482-5487.
62. Baran, P. S.; Guerrero, C. A.; Corey, E. J. Short, Enantioselective Total Synthesis of Okaramine N. J. Am. Chem. Soc. 2003, 125, 5628-5629.
63. Trost, B. M.; Quancard, J. Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1H-Indoles Using Trialkylboranes. J. Am. Chem. Soc. 2006, 128, 6314-6315.
64. Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. Pd-Catalyzed C3-Selective Allylation of Indoles with Allyl Alcohols Promoted by Triethylborane. J. Am. Chem. Soc. 2005, 127, 4592-4593.
65. Barton, D. H. R.; Crich, D.; Motherwell, W. B. The Invention of New Radical Chain Reactions. Part VIII. Radical Chemistry of Thiohydroxamic Esters; A New Method for the Generation of Carbon Radicals from Carboxylic Acids. Tetrahedron 1985, 41, 3901-3924.
66. Crich, D.; Fredette, E.; Flosi, W. J. Synthesis of the 3a-(3-Indolyl)-1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indole Core of Leptosins D-F. Heterocycles 1998, 48, 545-547.
67. Crich, D.; Natarajan, S. Chemistry of Cyclic Tautomers of Tryptophan: Free Radical Reactions at C-2 Occur Preferentially on the endo-Face of the Diazabicyclooctane Skeleton. J. Org. Chem. 1995, 60, 6237-6241.
68. Meza-Leon, R. L.; Crich, D.; Bernes, S.; Quintero, L. Endo-Selective Quenching of Hexahydropyrrolo[2,3-b]indole-Based N-Acyliminium Ions. J. Org. Chem. 2004, 69, 3976-3978.
69. Barton, D. H. R.; Crich, D.; Kretzschmar, G. The Invention of New Radical Chain Reactions. Part 9. Further Radical Chemistry of Thiohydroxamic Esters; Formation of Carbon-Carbon Bonds. J. Chem. Soc., Perkin Trans. 1 1986, 39-53.
70. Crich, D.; Banerjee, A. Unpublished results, University of Illinois at Chicago, 2006.
71. Renaud, P.; Seebach, D. Enantiomerically Pure Pyrrolidine Derivaxtives from trans-4-Hydroxy-L-Proline by Electrochemical Oxidative Decarboxylation and Titanium-tetrachloride-Mediated Reaction with Nucleophiles. Helv. Chim. Acta 1986, 69, 1704-1710.
72. Ungureanu, I.; Bologa, C; Chayer, S.; Mann, A. Phenylaziridine as a 1,3-Dipole. Application to the Synthesis of Functionalized Pyrrolidines. Tetrahedron Lett. 1999, 40, 5315-5318.
73. Larsen, C. H.; Rigdway, B. H.; Shaw, J. T.; Woerpel, K. A. A Stereoelectronic Model to Explain the Highly Stereoselective Reaction of Nucleophiles with Five-Membered-Ring Oxacarbenium Ions. J. Am. Chem. Soc. 1999, 121, 11208-11209.
74. Smith, D. M.; Tran, M. B.; Woerpel, K. A. Nucleophilic Addition to Fused Bicyclic Five-Membered Ring Oxacarbenium Ions: Evidence for Preferential Attack on the Inside Face. J. Am. Chem. Soc. 2003, 125, 14149-14152.