A chemoenzymatic synthesis of hept-6-ene-2,5-diol stereomers: Application to asymmetric synthesis of decarestrictine L, pyrenophorol, and stagonolide e

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 8067-8076

  Chatterjee, Sucheta ^a   Ghadigaonkar, Sneha ^a   Sur, Payel ^a   Sharma, Anubha ^a   Chattopadhyay, Subrata ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION;

ACYLATION REACTIONS; ASYMMETRIC SYNTHESIS; CHEMO-ENZYMATIC SYNTHESIS; CHIRAL INTERMEDIATES; LIPASE-CATALYZED; MACRODIOLIDE; SYNTHETIC PROTOCOLS; TETRAHYDROPYRAN;

REACTION INTERMEDIATES;

13 BENZYLOXY 10 METHYL 9 OXA 8 OXOPENTA 6,14 DIENE 2,5 DIOL; 2 ACRYLOXY 13 BENZYLOXY 10 METHYL 9 OXA 8 OXOPENTA 6,14 DIEN 5 OL; 3 ACETOXY 6 4 METHOXYBENZYLOXYHEPT 1 ENE; 3 ACETOXY 6 TERT BUTYLDIPHENYLSILYLOXYHEPT 1 ENE; 3 BENZYLOXY 11 TERT BUTYLDIMETHYLSILYLOXY 14 TERT BUTYLDIPHENYLSILYLOXY 6 METHYL 7 OXA 8 OXOPENTA 1,9 DIENE; 3 BENZYLOXY 6 TERT BUTYLDIPHENYLSILYLOXYHEPT 1 ENE; 4 4 METHOXYBENZYLOXYPENTANAL; 4 HYDROXY 7 4 METHOXYBENZYLOXYOCT 2 ENAL; 4 TERT BUTYLDIMETHYLSILYLOXY 7 TERT BUTYLDIPHENYLSILYLOXYOCT 2 ENOIC ACID; 4 TERT BUTYLDIPHENYLSILYLOXYPENTANAL; 5 BENZYLOXYHEPT 6 EN 2 OL; 6 4 METHOXYBENZYLOXY 2 METHYLHEPT 2 ENE; 6 4 METHOXYBENZYLOXYHEPT 1 EN 3 OL; 6 ACETOXY 2 METHYL 2 HEPTENE; 6 METHYL 5 HEPTEN 2 OL; 6 TERT BUTYLDIPHENYLSILYLOXY 2 METHYL 2 HEPTENE; 6 TERT BUTYLDIPHENYLSILYLOXYHEPT 1 EN 3 OL; 8 TERT BUTYLDIPHENYLSILYLOXY 5 HYDROXYNON 3 EN 2 ONE; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; DECARESTRICTINE L; ETHYL 4 HYDROXY 7 TERT BUTYLDIPHENYLSILYLOXYOCT 2 ENOATE; ETHYL 4 TERT BUTYLDIMETHYLSILYLOXY 7 TERT BUTYLDIPHENYLSILYLOXYOCT 2 ENOATE; IMMUNOMODULATING AGENT; MACROLIDE; PYRENOPHOROL; PYRENOPHOROL MONOBENZYL ETHER; STAGONOLIDE E; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; HETEROCYCLIC COMPOUND; KETONE; LACTONE; PYRAN DERIVATIVE; SINGLE HETEROCYCLIC RINGS; STAGONOLIDE; TRIACYLGLYCEROL LIPASE;

ACYLATION; ALKYNYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

ACYLATION; CATALYSIS; HETEROCYCLIC COMPOUNDS; HETEROCYCLIC COMPOUNDS, 1-RING; KETONES; LACTONES; LIPASE; MACROLIDES; MOLECULAR STRUCTURE; PYRANS; STEREOISOMERISM;

EID: 84924308725     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5012575     Document Type: Article

References (104)

1. Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44-122
2. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-340
3. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. Michels, P. C.; Khmelnitsky, Y. L.; Dordick, J. S.; Clark, D. S. Trends Biotechnol. 1998, 16, 210-215
5. Fessner, W.-D.; Helaine, V. Curr. Opin. Biotechnol. 2001, 12, 574-586
6. Clouthierzab, C. M.; Pelletier, J. N. Chem. Soc. Rev. 2012, 41, 1585-1605
7. Reetz, M. T. J. Am. Chem. Soc. 2013, 135, 12480-12496
8. Nestl, B. M.; Hammer, S. C.; Nebel, B. A.; Hauer, B. Angew. Chem., Int. Ed. 2014, 53, 3070-3095
9. Reetz, M. T. Curr. Opin. Chem. Biol. 2002, 6, 145-150
10. Faber, K. Biotransformations in Organic Chemistry, 5th ed.; Springer: Heidelberg, Germany, 2004.
11. Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolases in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2005.
12. Gotor-Fernández, V.; Busto, E.; Gotor, V. Adv. Synth. Catal. 2006, 797-812
13. Haraldsson, G. G. The Application of Lipases in Organic Synthesis [Online]; John Wiley & Sons, Ltd.: Hoboken, NJ, 2010. DOI: 10.1002/9780470772508.ch24.
14. Sharma, S.; Kanwar, S. S. Sci. World J. 2014, 2014 625258
15. Sharma, A.; Chattopadhyay, S. J. Org. Chem. 1998, 63, 6128-6131
16. Sharma, A.; Chattopadhyay, S. J. Org. Chem. 1999, 64, 8059-8062
17. Kulkarni, B. A.; Sharma, A.; Gamre, S.; Chattopadhyay, S. Synthesis 2003, 595-599
18. Kumar, A. N.; Bhatt, S.; Chattopadhyay, S. Tetrahedron: Asymmetry 2009, 20, 205-209
19. Sharma, A.; Gamre, S.; Chattopadhyay, S. Tetrahedron: Asymmetry 2009, 20, 1164-1167
20. Ghadigaonkar, S.; Koli, M. R.; Gamre, S. S.; Choudhary, M. K.; Chattopadhyay, S.; Sharma, A. Tetrahedron: Asymmetry 2012, 23, 1093-1099
21. Maity, B.; Chattopadhyay, S. Curr. Bioact. Compd. 2008, 4, 225-244
22. Guha, P.; Dey, A.; Sarkar, B.; Dhyani, M. V.; Chattopadhyay, S.; Bandyopadhyay, S. K. J. Pharmacol. Exp. Ther. 2009, 328, 1-10
23. Guha, P.; Dey, A.; Chatterjee, A.; Chattopadhyay, S.; Bandyopadhyay, S. K. Br. J. Pharmacol. 2010, 159, 726-734
24. Patro, B. S.; Maity, B.; Chattopadhyay, S. Antioxid. Redox Signaling 2010, 12, 945-960
25. Patro, B. S.; Tyagi, M.; Saha, J.; Chattopadhyay, S. Bioorg. Med. Chem. 2010, 18, 7043-7051
26. Yadav, S. K.; Adhikary, B.; Chand, S.; Maity, B.; Bandyopadhyay, S. K.; Chattopadhyay, S. Free Radical Biol. Med. 2012, 52, 1175-1187
27. Maity, B.; Yadav, S. K.; Patro, B. S.; Bandyopadhyay, S. K.; Chattopadhyay, S. Free Radical Biol. Med. 2012, 52, 1680-1691
28. Grabley, S.; Hammann, P.; Hutter, K.; Kirsch, R.; Kluge, H.; Thiericke, R.; Mayer, M.; Zeeck, A. J. Antibiot. 1992, 45, 1176-1182
29. Grabley, S.; Granzer, E.; Hutter, K.; Ludwig, D.; Mayer, M.; Thiericke, R.; Till, G.; Wink, J.; Philipps, S.; Zeeck, A. J. Antibiot. 1992, 45, 56-65
30. Kis, Z.; Furger, P.; Sigg, H. P. Experientia 1969, 25, 123-124
31. Nozoe, S.; Hirai, K.; Tsuda, K.; Ishibashi, K.; Shirasak, M. Tetrahedron Lett. 1965, 4675-4677
32. Grove, J. F. J. Chem. Soc. 1971, 12, 2261-2263
33. Kind, R.; Zeeck, A.; Grabley, S.; Thiericke, R.; Zerlin, M. J. Nat. Prod. 1996, 59, 539-540
34. Evidente, A.; Capasso, R.; Andolfi, A.; Vurro, M.; Chiara Zonno, M. Nat. Toxins 1999, 6, 183
35. Evidente, A.; Cimmino, A.; Berestetskiy, A.; Mitina, G.; Andolfi, A.; Motta, A. J. Nat. Prod. 2008, 71, 31-34
36. Kastanias, M. A.; Chrysayi-Tokousbalides, M. Pest Manage. Sci. 2000, 56, 227-232
37. Karsten, K.; Umar, F.; Ulrich, F.; Barbara, S.; Siegfried, D.; Gennaro, P.; Piero, S.; Sándor, A.; Tibor, K. Eur. J. Org. Chem. 2007, 3206-3211
38. Zhang, W.; Krohn, K.; Egold, H.; Draeger, S.; Schulz, B. Eur. J. Org. Chem. 2008, 4320-4328
39. Kind, R.; Zeeck, A.; Grabley, S.; Thiericke, R.; Zerlin, M. J. Nat. Prod. 1996, 59, 539-540
40. Christner, C.; Kullertz, G.; Fischer, G.; Zerlin, M.; Grabley, S.; Thiericke, R.; Taddei, A.; Zeeck, A. J. Antibiot. 1998, 51, 368-371
41. Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 5739-5742
42. Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381-6382
43. Nokami, J.; Taniguchi, T.; Ogawa, Y. Chem. Lett. 1995, 24, 43-44
44. Solladie, G.; Arce, E.; Bauder, C.; Carreno, M. C. J. Org. Chem. 1998, 63, 2332-2337
45. Esumi, T.; Kimura, R.; Mori, M.; Iwabuchi, Y.; Irie, H.; Hatakeyama, S. Heterocycles 2000, 52, 525-528
46. Lukesh, J. M.; Donaldson, W. A. Tetrahedron: Asymmetry 2003, 14, 757-762
47. Clark, J. S.; Fessard, T. C.; Whitlock, G. A. Tetrahedron 2006, 62, 73-78
48. Garcia, I.; Gomez, G.; Teijeira, M.; Teran, C.; Fall, Y. Tetrahedron Lett. 2006, 47, 1333-1335
49. Riatto, V. B.; Pilli, R. A.; Victor, M. M. Tetrahedron 2008, 10, 2279-2300
50. Rawat, V.; Chouthaiwale, P. V.; Suryavanshi, G.; Sudalai, A. Tetrahedron: Asymmetry 2009, 20, 2173-2177
51. Zúñiga, A.; Pérez, M.; Pazos, G.; Gómez, G.; Fall, Y. Synthesis 2010, 2446-2450
52. Dommerholdt, E. J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1991, 32, 1499-1502
53. Machinaga, N.; Kibayashi, C. Tetrahedron Lett. 1993, 34, 841-844
54. Amigoni, S.; Le Floch, Y. Tetrahedron: Asymmetry 1997, 8, 2827-2831
55. Yadav, J. S.; Reddy, U. V. S.; Reddy, B. V. S. Tetrahedron Lett. 2009, 50, 5984-5986
56. Oh, H.-S.; Kang, H.-Y. Bull. Korean Chem. Soc. 2011, 32, 2869-2870
57. Yadav, J. S.; Reddy, G.; Rao, T. S.; Reddy, B. V. S.; Ghamdi, A. A. K. A. Synthesis 2012, 783-787
58. Trost, B. M.; Quintard, A. Angew. Chem., Int. Ed. 2012, 51, 6704-6708
59. Sabitha, G.; Padmaja, P.; Reddy, P. N.; Jadav, S. S.; Yadav, J. S. Tetrahedron Lett. 2010, 51, 6166-6168
60. Das, T.; Nanda, S. Tetrahedron Lett. 2012, 53, 256-258
61. Schmidt, B.; Kunz, O. Beilstein J. Org. Chem. 2013, 9, 2544-2555
62. Sharma, A.; Gamre, S.; Chattopadhyay, S. Tetrahedron: Asymmetry 2009, 20, 1164-1167
63. Sharma, A.; Mahato, S.; Chattopadhyay, S. Tetrahedron Lett. 2009, 50, 4986-4988
64. Biswas, S.; Chattopadhyay, S.; Sharma, A. Tetrahedron: Asymmetry 2010, 21, 27-32
65. Ohtani, T.; Nakatsukasa, H.; Kamezawa, M.; Tachibana, H.; Naoshima, Y. J. Mol. Catal. B: Enzym. 1998, 4, 53-60
66. Fuji, M.; Fukumura, M.; Hory, Y.; Hirai, Y.; Akita, H.; Nakamura, K.; Toriizuka, K.; Ida, Y. Tetrahedron: Asymmetry 2006, 17, 2292-2298
67. Felluga, F.; Forzato, C.; Ghelfi, F.; Nitti, P.; Pitacco, G.; Pagnoni, U. M.; Roncaglia, F. Tetrahedron: Asymmetry 2007, 18, 527-536
68. Mori, K. Tetrahedron 1981, 37, 1341-1342
69. Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1995, 51, 8799-8808
70. Kinoshita, M.; Ohno, A. Tetrahedron 1996, 52, 5397-5406
71. Steinreiber, A.; Stadler, A.; Mayer, S. F.; Faber, K.; Kappe, C. O. Tetrahedron Lett. 2001, 42, 6283-6286
72. Steinreiber, A.; Edegger, K.; Mayer, S. F.; Faber, K. Tetrahedron: Asymmetry 2001, 12, 2067-2071
73. Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P.; Fontana, S. Tetrahedron: Asymmetry 2000, 11, 2367-2373
74. Belan, A.; Bolte, J.; Fauve, A.; Gourcy, J. G.; Veschambre, H. J. Org. Chem. 1987, 52, 256-260
75. Fantin, G.; Fogagnolo, M.; Giovannini, P. P.; Medici, A.; Pedrini, P. Tetrahedron: Asymmetry 1995, 6, 3047-3053
76. Clair, N. S.; Wang, Y.-F.; Margolin, A. L. Angew. Chem. 2000, 112, 388-391
77. Chen, S. L.; Hu, Q. Y.; Loh, T. P. Org. Lett. 2004, 6, 3365-3367
78. Dale, J. A.; Mosher, S. H. J. Am. Chem. Soc. 1973, 95, 512-519
79. Patil, P. N.; Chattopadhyay, A.; Udupa, S. R.; Banerji, A. Biotechnol. Lett. 1993, 15, 367-372
80. Ferreira, H. V.; Rocha, L. C.; Severino, R. P.; Viana, R. B.; da Silva, A. B. F.; Porto, A. L. M. J. Iran. Chem. Soc. 2010, 7, 883-889
81. Burgess, K.; Henderson, I. Tetrahedron: Asymmetry 1990, 1, 57-60
82. Jana, N.; Mahapatra, T.; Nanda, S. Tetrahedron: Asymmetry 2009, 20, 2622-2628
83. Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665
84. Cabrera, Z.; Fernandez-Lorente, G.; Fernandez-Lafuente, R.; Palomo, J. M.; Guisan, J. M. J. Mol. Catal. B: Enzym. 2009, 57, 171-176
85. Enders, D.; Nguyen, D. Synthesis 2000, 2092-2098
86. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388
87. Schrock, R. R. Tetrahedron 1999, 55, 8141-8153
88. Blackwell, H. E.; OLeary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71
89. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043
90. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29
91. Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923
92. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527
93. Lin, Y. A.; Davis, B. G. Beilstein J. Org. Chem. 2010, 6, 1219-1228
94. Galan, B. R.; Kalbarczyk, K. P.; Szczepankiewicz, S.; Keister, J. B.; Diver, S. T. Org. Lett. 2007, 9, 1203-1206
95. Lipshutz, B. H.; Aquinaldo, G. T.; Ghorai, S.; Voigtritter, K. Org. Lett. 2008, 10, 1325-1328
96. Ferrié, L.; Bouzbouz, S.; Cossy, J. Org. Lett. 2009, 11, 5446-5448
97. Voigtritter, K.; Ghorai, S.; Lipshutz, B. H. J. Org. Chem. 2011, 76, 4697-4702
98. Meek, S. J.; OBrien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471 (7339) 461-466
99. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370
100. Sundby, E.; Perk, L.; Anthonsen, T.; Aasen, A. J.; Hansen, T. V. Tetrahedron 2004, 60, 521-524
101. Simpson, T. J. Nat. Prod. Rep. 1987, 4, 339-376
102. Mori, K. Tetrahedron 1989, 45, 3233-3298
103. Gurjar, M. K.; Nagaprasad, R.; Ramana, C. V. Tetrahedron Lett. 2003, 44, 2873-2875
104. Ando, K. J. Org..Chem. 1997, 62, 1934-1939