A general approach to chiral building blocks via direct amino acid-catalyzed cascade three-component reductive alkylations: Formal total synthesis of HIV-1 protease inhibitors, antibiotic agglomerins, brefeldin A, and (R)-γ-hexanolide

Journal of Organic Chemistry

Volumn 75, Issue 1, 2010, Pages 74-85

  Ramachary, Dhevalapally B ^a   Reddy, Y Vijayendar ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; AGGLOMERINS; CHEMICAL EQUATIONS; CHIRAL ALDEHYDE; CHIRAL BUILDING BLOCKS; DIASTEREOSELECTIVITIES; DIAZOMETHANES; FUNCTIONALIZED; GENERAL APPROACH; HIGH YIELD; HIV-1 PROTEASE INHIBITORS; L-PROLINE; METHYL VINYL KETONES; REDUCTIVE ALKYLATION; ROBINSON ANNULATION; SEQUENTIAL COMBINATION; THREE-COMPONENT; TOTAL SYNTHESIS;

ACETYLENE; ALDEHYDES; ALKYLATION; AMINO ACIDS; ESTERIFICATION; ESTERS; KETONES; LIGHTING; OLEFINS; ORGANIC ACIDS; VIRUSES;

SYNTHESIS (CHEMICAL);

ACETONE; ACETYLENE; AGGLOMERIN A; AGGLOMERIN B; AGGLOMERIN C; AGGLOMERIN D; ALDEHYDE; ALKENE; AMINO ACID; BREFELDIN A; BRONSTED ACID; CARBONYL DERIVATIVE; GAMMA HEXANOLIDE; GLYCERALDEHYDE; HEXANE; PHOSPHOLIPASE A2 INHIBITOR; PROLINE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ESTERIFICATION; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; LACTONIZATION; MICHAEL ADDITION; NONHUMAN; RACEMIZATION; REDUCTION; ROBINSON ANNULATION; STEREOCHEMISTRY;

4-BUTYROLACTONE; ALKYLATION; AMINO ACIDS; ANTI-BACTERIAL AGENTS; BREFELDIN A; CATALYSIS; DRUG DESIGN; ESTERIFICATION; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; KETONES; LACTONES; STEREOISOMERISM;

EID: 73449140458     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901799n     Document Type: Article

References (112)

1. (a) Yamashita, M.; Murai, H.; Mittra, A.; Yoshioka, T.; Kawasaki, I.; Gotoh, M.; Higashi, T.; Hatsuyama, R.; Ohta, S. Heterocycles 1998, 48, 2327-2337.
2. (b) Schobert, R.; Jagusch, C. J. Org. Chem. 2005, 70, 6129-6132.
3. (c) Zhdankina, G. M.; Serebryakov, E. P. Russ. Chem. Bull. 1985, 34, 2414-2415.
4. (d) Kitahara, T.; Mori, K. Tetrahedron 1984, 40, 2935-2944.
5. (e) Ariza, J.; Font, J.; Ortuno, R. M. Tetrahedron Lett. 1991, 32, 1979-1982.
6. (f) Kotkar, S. P.; Suryavanshi, G. S.; Sudalai, A. Tetrahedron: Asymmetry 2007, 18, 1795-1798.
7. (g) Uchida, I.; Ezaki, M.; Shigematsu, N.; Hashimoto, M. J. Org. Chem. 1985, 50, 1342-1344.
8. (h) Bernardo, S. D.; Tengi, J. P.; Sasso, G. J.; Weigele, M. J. Org. Chem. 1985, 50, 3457-3462.
9. (i) Sodeoka, M.; Sarape, R.; Kagamizono, T.; Osada, H. Tetrahedron Lett. 1996, 37, 8775-8778.
10. (j) Ray, N. C.; et al. Bioorg. Med. Chem. Lett. 2007, 17, 4901-4905.
11. (k) Huntington, K. M.; Yi, T.; Wei, Y.; Pei, D. Biochemistry 2000, 39, 4543-4551.
12. (l) Lu, D.; Vince, R. Bioorg. Med. Chem. Lett. 2007, 17, 5614-5619.
13. (m) Anderluh, P. S.; Anderluh, M.; Ilaš, J.; Mravljak, J.; Dolenc, M. S.; Stegnar, M.; Kikelj, D. J. Med. Chem. 2005, 48, 3110-3113.
14. (n) Wu, Z.; Minhas, G. S.; Wen, D.; Jiang, H.; Chen, K.; Zimniak, P.; Zheng, J. J. Med. Chem. 2004, 47, 3282-3294.
15. (o) Bohme, T. M.; Keim, C.; Kreutzmann, K.; Linder, M.; Dingermann, T.; Dannhardt, G.; Mutschler, E.; Lambrecht, G. J. Med. Chem. 2003, 46, 856-867.
16. (p) Howard, J. B.; Nelsestuen, G. L. Biochem. Biophys. Res. Commun. 1974, 59, 757-763.
17. (q) Nelsestuen, G. L.; Zytkovicz, T. H. J. Biol. Chem. 1974, 249, 6347-6350.
18. (r) Zytkovicz, T. H.; Nelsestuen, G. L. J. Biol. Chem. 1975, 250, 2968-2972.
19. (s) Stenflo, J.; Fernlund, P.; Egan, W.; Roepstorff, P. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 2730-2733.
20. (t) Saito, H.; Hirata, T. TetrahedronLett. 1987, 28, 4065-4068.
21. (u) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669-1730.
22. (a) Jiang, S.; Lai, C. C.; Kelley, J. A.; Roller, P. P. Tetrahedron Lett. 2006, 47, 23-25.
23. (b) Quaedflieg, P. J. L. M.; Kesteleyn, B. R. R.; Wigerinck, P. B. T. P.; Goyvaerts, N. M. F.; Vijn, R. J.; Liebregts, C. S. M.; Kooistra, J. H. M. H.; Cusan, C. Org. Lett. 2005, 7, 5917-5920.
24. (c) Suarez, R. M.; Sestelo, J. P.; Sarandeses, L. A. Chem. - Eur. J. 2003, 9, 4179-4187.
25. (d) Ngai, M. -Y.; Kong, J. -R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063-1072.
26. (e) Krief, A.; Dumont, W.; Baillieul, D. Tetrahedron Lett. 2005, 46, 8033-8035.
27. (f) Kesteleyn, B. R. R.; Surleraux, D. L. N. G. PCT Int. Appl. 2003, 47 pp. CODEN: PIXXD2 WO 2003022853 A1 20030320, CAN 138:238003 (patent written in English).
28. (g) Krief, A.; Provins, L.; Froidbise, A. Synlett 1999, 1936-1938.
29. (h) Ma, D.; Cao, Y.; Yang, Y.; Cheng, D. Org. Lett. 1999, 1, 285-287.
30. For recent papers on organocatalytic TCRA reactions for C-C/C-H bond formation, see: (a) Ramachary, D. B.; Kishor, M. J. Org. Chem. 2007, 72, 5056-5068.
31. (b) Ramachary, D. B.; Kishor, M. Org. Biomol. Chem. 2008, 6, 4176-4187.
32. (c) Ramachary, D. B.; Venkaiah, C.; Reddy, Y. V.; Kishor, M. Org. Biomol. Chem. 2009, 7, 2053-2062. For recent papers on organocatalytic reductions for C-H bond formation, see:
33. (d) Yang, J. W.; Fonseca, M. T. H.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660-6662.
34. (e) Yang, J. W.; Fonseca, M. T. H.; Vignola, N.; List, B. Angew. Chem Int. Ed. 2005, 44, 108-110.
35. (f) Mayer, C.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193-4195.
36. (g) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368-13369.
37. (h) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32-33.
38. (i) Tuttle, J. B.; Quellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662-12663. For recent papers on organocatalytic reductions for C-N bond formation, see:
39. (j) Hofmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424-7426.
40. (k) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84-86.
41. (l) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781-3783.
42. (m) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751-6755.
43. (n) Ouellet, S. G.; Walji, A. M.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327-1339.
44. (o) You, S. -L. Chem. Asian. J. 2007, 2, 820-827. For recent papers on organocatalytic reductions for C-O bond formation, see:
45. (p) Yang, J. W.; List, B. Org. Lett. 2006, 8, 5653-5655.
46. For the recent papers on observation of organocatalytic racemization/ epimerizations, see: (a) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F. III. Tetrahedron Lett. 2002, 43, 9591-9595.
47. (b) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. III. Synlett 2003, 12, 1910-1914.
48. (c) Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F. III. J. Org. Chem. 2004, 69, 5838-5849.
49. (d) Couturier, C.; Liron, M.; Schlama, T.; Zhu, J. Synlett 2005, 5, 851-853.
50. (e) Ramachary, D. B.; Reddy, Y. V.; Prakash, B. V. Org. Biomol. Chem. 2008, 6, 719-726.
51. For recent reviews on organocatalytic cascade and multicomponent reactions, see: (a) Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354-366.
52. (b) Pellissier, H. Tetrahedron 2006, 62, 2143-2173.
53. (c) Chapman, C. J.; Frost, C. G. Synthesis 2007, 1-21.
54. (d) Gerencser, J.; Dorman, G.; Darvas, F. QSAR Comb. Sci. 2006, 25, 439-448.
55. (e) Guillena, G.; Ramon, D. J.; Yus, M. Tetrahedron: Asymmetry 2007, 18, 693-700.
56. (f) Enders, D.; Grondal, C.; Huettl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581.
57. (g) Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416-5470.
58. (h) Notz, W.; Tanaka, F.; Barbas, C. F. III. Acc. Chem. Res. 2004, 37, 580-591. For selected recent papers on organocatalytic cascade reactions from our group, see:
59. (i) Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. J. Org. Chem. 2007, 72, 1458-1463.
60. (j) Ramachary, D. B.; Sakthidevi, R. Chem. - Eur. J. 2009, 15, 4516-4522. For selected recent papers on organocatalytic cascade reactions from other research groups, see:
61. (k) Ramachary, D. B.; Barbas, C. F. III. Chem.- Eur. J. 2004, 10, 5323-5331.
62. (l) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036-15037.
63. (m) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051-15053.
64. (n) Marigo, M.; Bertelsen, S.; Landa, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2006, 128, 5475-5479.
65. (o) Enders, D.; Huettl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861-863.
66. (p) Rios, R.; Sunden, H.; Ibrahem, I.; Zhao, G.-L.; Cordova, A. Tetrahedron Lett. 2006, 47, 8679-8682.
67. (q) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354-10355.
68. (r) Tejedor, D.; Gonzalez-Cruz, D.; Santos-Exposito, A.; Marrero-Tellado, J. J.; de Armas, P.; Garcia-Tellado, F. Chem. - Eur. J. 2005, 11, 3502-3510.
69. (s) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683-3686.
70. (t) Ishikawa, H.; Suzuki, T.; Hayashi, Y. Angew. Chem., Int. Ed. 2009, 48, 1304-1307.
71. (u) Zhu, D.; Lu, M.; Chua, P. J.; Tan, B.; Wang, F.; Yang, X.; Zhong, G. Org. Lett. 2008, 10, 4585-4588.
72. (a) Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Chem. Rev. 2004, 104, 3059-3077.
73. (b) Atwal, K. S.; Wang, P.; Rogers, W. L.; Sleph, P.; Monshizadegan, H.; Ferrara, F. N.; Traeger, S.; Green, D. W.; Grover, G. J. J. Med. Chem. 2004, 47, 1081-1084.
74. (c) Frederick, R.; Robert, S.; Charlier, C.; Ruyck, J.; Wouters, J.; Pirotte, B.; Masereel, B.; Pochet, L. J. Med. Chem. 2005, 48, 7592-7603.
75. (d) Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett. 2003, 5, 4481-4484.
76. (e) Ross, S. A.; Sultana, G. N. N.; Burandt, C. L.; ElSohly, M. A.; Marais, J. P. J.; Ferreira, D. J. Nat. Prod. 2004, 67, 88-90.
77. (f) Burlison, J. A.; Neckers, L.; Smith, A. B.; Maxwell, A.; Blagg, B. S. J. J. Am. Chem. Soc. 2006, 128, 15529-15536.
78. (g) Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499-1504.
79. (h) Wijeratne, E. M. K.; Turbyville, T. J.; Fritz, A.; Whitesell, L.; Gunatilaka, A. A. L. Bioorg. Med. Chem. 2006, 14, 7917-7923.
80. (i) Rezanka, T.; Sigler, K. J. Nat. Prod. 2007, 70, 1487-1491.
81. (j) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939-9953.
82. For the selected reviews on quaternary carbon generation, see: (a) Austeri, M.; Buron, F.; Constant, S.; Lacour, J.; Linder, D.; Muller, J.; Tortoioli, S. Pure Appl. Chem. 2008, 80, 967-977.
83. (b) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186.
84. (c) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-5367.
85. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
86. (e) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
87. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
88. (g) Srikrishna, A.; Krishnan, K.; Nagaraju, S. J. Indian Inst. Sci. 1994, 74, 157-168.
89. (h) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569.
90. For HMPT-catalyzed Michael reactions, see: Grossman, R. B.; Comesse, S.; Rasne, R. M.; Hattori, K.; Delong, M. N. J. Org. Chem. 2003, 68, 871-874.
91. Applications of Wieland-Miescher (W-M) ketone analogues; see: (a) Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357.
92. (b) Deng, W.; Jensen, M. S.; Overman, L. E.; Rucker, P. V.; Vionnet, J.-P. J. Org. Chem. 1996, 61, 6760-6761.
93. (c) Katoh, T.; Nakatani, M.; Shikita, S.; Sampe, R.; Ishiwata, A.; Ohmori, O.; Nakamura, M.; Terashima, S. Org. Lett. 2001, 3, 2701-2704.
94. (d) Inomata, K.; Barrague, M.; Paquette, L. A. J. Org. Chem. 2005, 70, 533-539.
95. (e) Nagamine, T.; Inomata, K.; Endo, Y.; Paquette, L. A. J. Org. Chem. 2007, 72, 123-131. Applications of Hajos-Parrish (H-P) ketone analogues; see:
96. (f) Majetich, G.; Song, J. S.; Ringold, C.; Nemeth, G. A.; Newton, M. G. J. Org. Chem. 1991, 56, 3973-3988.
97. (g) Ruprah, P. K.; Cros, J. -P.; Pease, J. E.; Whittingham, W. G.; Williams, J. M. J. Eur. J. Org. Chem. 2002, 3145-3152.
98. (h) Cao, L.; Sun, J.; Wang, X.; Zhu, R.; Shi, H.; Hu, Y. Tetrahedron 2007, 63, 5036-5041.
99. (i) Kasch, H.; Liedtke, B.; U. S. Pat. Appl. Publ. 2006, 24 pp, CODEN: USXXCO US 2006089340 A1 20060427, CAN 144:433022 (patent written in English).
100. (j) Sevillano, L. G.; Melero, C. P.; Boya, M.; Lopez, J. L.; Tome, F.; Caballero, E.; Carron, R.; Montero, M. J.; Medarde, M.; San Feliciano, A. Bioorg. Med. Chem. 1999, 7, 2991-3001. For the pharmaceutical applications of W-M and H-P ketone analogues, see:
101. (k) Thompson, C. F.; Quraishi, N.; Ali, A.; Mosley, R. T.; Tata, J. R.; Hammond, M. L.; Balkovec, J. M.; Einstein, M.; Ge, L.; Harris, G.; Kelly, T. M.; Mazur, P.; Pandit, S.; Santoro, J.; Sitlani, A.; Wang, C.; Williamson, J.; Miller, D. K.; Yamin, T. D.; Thompson, C. M.; O'Neill, E. A.; Zaller, D.; Forrest, M. J.; Carballo-Jane, E.; Luell, S. Bioorg. Med. Chem. Lett. 2007, 17, 3354-3361.
102. (l) Smith, C. J.; Ali, A.; Balkovec, J. M.; Graham, D. W.; Hammond, M. L.; Patel, G. F.; Rouen, G. P.; Smith, S. K.; Tata, J. R.; Einstein, M.; Ge, L.; Harris, G. S.; Kelly, T. M.; Mazur, P.; Thompson, C. M.; Wang, C. F.; Williamson, J. M.; Miller, D. K.; Pandit, S.; Santoro, J. C.; Sitlani, A.; Yamin, T. D.; O'Neill, E. A.; Zaller, D. M.; Carballo-Jane, E.; Forrest, M. J.; Luell, S. Bioorg. Med. Chem. Lett. 2005, 15, 2926-2931.
103. (m) Ali, A.; Balkovec, J. M.; Beresis, R.; Colletti, S. L.; Graham, D. W.; Patel, G. F.; Smith, C. J. PCT Int. Appl. 2004, CODEN: PIXXD2WO2004093805 A2 20041104, CAN141:395547, (in English; 201 pp).
104. (a) Zhong, G.; Hoffmann, T.; Lerner, R. A.; Danishefsky, S.; Barbas, C. F. III. J. Am. Chem. Soc. 1997, 119, 8131-8132.
105. (b) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273-11283.
106. (c) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 12911-12912.
107. (d) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17.
108. (e) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479.
109. (f) List, B.; Hoang, L.; Martin, H. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5839-5842.
110. (g) Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558-569.
111. CCDC-743987 for (-)-13bkb contains the supplementary crystallographic data for this paper. This data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or mail to: deposit@ccdc.cam.ac.uk.
112. For the total synthesis of natural products through cascade reactions, see: Nicolaou, K. C.; Chen, J. S. Chem. Soc. Rev. 2009, 38, 2993-3009. and references cited therein.