An approach to lauroxanes by iterative use of Co2(CO) 6-acetylenic complexes. A formal synthesis of (+)-laurencin

Journal of Organic Chemistry

Volumn 75, Issue 19, 2010, Pages 6660-6672

  Ortega, Nuria ^a   Martín, Victor S ^a   Martín, Tomás ^a,b  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPLEXES; CYCLIC ETHER; FORMAL SYNTHESIS; MONTMORILLONITE K10; NEW APPROACHES; NICHOLAS REACTIONS; NINE-MEMBERED RINGS; RED ALGAE; RING CLOSING METATHESIS;

ALGAE; CLAY MINERALS; COBALT; COMPLEXATION; ETHERS; ORGANIC COMPOUNDS; SILICATE MINERALS; SYNTHESIS (CHEMICAL);

COBALT COMPOUNDS;

2 ETHYL 7 HEXYL 2,3,4,7 TETRAHYDROOXEPINE; 2 ETHYL 8 [(((TRIMETHYLSILYL) ETHYNYL) 3,4,7,8 TETRAHYDRO 2H OXOCIN 3 YL) OXY] DIPHENYLSILANE; 2 ETHYNYL 7 HEXYL 2,3,4,7 TETRAHYDROOXEPINE; 2 ETHYNYL 8 HEXYL 3,4,7,8 TETRAHYDRO 2H OXOCINE; 4 [(TERT BUTYLDIPHENYLSILYL) OXY] HEPT 6 EN 3 OL; 5 (BENZYLOXY) HEPT 1 EN 4 YL) OXY] TETRAHYDRO 2H PYRAN; 5 ETHYL 4 [(TETRAHYDRO 2H PYRAN 2 YL) OXY] DIHYDROFURAN 2(3H) ONE; 5,8 DIALLYL 7 ETHYL 2,2,11,11 TETRAMETHYL 10,10 DIPHENYL 6,9 DIOXA 2,10 DISILADODEC 3 YNE; 6 BROMO 1 (TRIMETHYLSILYL) HEX 1 YN 3 OL; 7 [((TERT BUTYLDIMETHYLSILYL) OXY) 8 ETHYL 3,6,7,8 TETRAHYDRO 2H OXOCIN 2 YL] PROP 2 EN 1 OL; 7 [((TERT BUTYLDIPHENYLSILYL) OXY) 8 ETHYL 3,6,7,8 TETRAHYDRO 2H OXOCIN 2 YL] PROP 2 EN 1 OL; 7 [((TERT BUTYLDIPHENYLSILYL) OXY) 8 ETHYL 3,6,7,8 TETRAHYDRO 2H OXOCIN 2 YL] PROP 2 YN 1 OL; 8 ALLYL 5 (3 BROMOPROPYL) 7 ETHYL 2,2,11,11 TETRAMETHYL 10,10 DIPHENYL 6,9 DIOXA 2,10 DISILADODEC 3 YNE; [(5 (BENZYLOXY) HEPT 1 EN 4 YL) OXY] (TERT BUTYL) DIPHENYLSILANE; [(8 HEXYL 3,4,7,8 TETRAHYDRO 2H OXOCIN 2 YL) ETHYNYL) TRIMETHYLSILANE; [(8R HEXYL 3,4,7,8 TETRAHYDRO 2H OXOCIN 2 YL) ETHYNYL] TRIMETHYLSILANE; [(9 BUTYL 2,3,4,7,8,9 HEXAHYDROOXONIN 2 YL) ETHYNYL] TRIMETHYLSILANE; [(DEC 1 EN 43 YLOXY) HEPT 6 EN 1 YN 1 YL] TRIMETHYLSILANE; [(TETRAHYDRO 2H PYRAN 2 YL) OXY] HEPT 6 EN 3 OL; ACETYLENE; ACETYLENE DERIVATIVE; CARBON DIOXIDE; COBALT COMPLEX; DEXTRO CIS LAUTHISAN; ETHER DERIVATIVE; LAUROXANE DERIVATIVE; MONTMORILLONITE; NATURAL PRODUCT; TRIMETHYL [3 (NON 1 EN 5 YLOXY) HEPT 6 EN 1 YN 1 YL] SILANE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; ISOMERIZATION; NONHUMAN; RED ALGA; RING CLOSING METATHESIS; SYNTHESIS;

ALKYNES; COBALT; CYCLIZATION; FATTY ACIDS, UNSATURATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXOCINS; STEREOISOMERISM;

EID: 77957137365     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101566x     Document Type: Article

References (97)

1. Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 1, pp 43 - 121.
2. Erickson, K. L. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; Vol. V, pp 131 - 257.
3. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909
4. Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48 and preceding issues
5. Kurozawa, E.; Fukuzawa, A.; Irie, T. Tetrahedron Lett. 1972, 2121-2124
6. Alvarez, E.; Candenas, M. L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980
7. Mori, Y. Chem.-Eur. J. 1997, 3, 849-852
8. Hoberg, L. O. Tetrahedron 1998, 54, 12631-12670
9. Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44-122
10. Marmsäter, F. P.; West, F. G. Chem.-Eur. J. 2002, 8, 4346-4353
11. For representative examples, see: Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566
12. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126
13. Linderman, R. J.; Siedlecki, J.; ONeill, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919-6920
14. Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549
15. Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904-1907
16. Kadota, I.; Uyehara, H.; Yamamoto, Y. Tetrahedron 2004, 60, 7361-7365
17. Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2004, 126, 12432-12440
18. Crimmins, M. T.; She, J. J. Am. Chem. Soc. 2004, 126, 12790-12791
19. Clark, J. S.; Kimber, M. C.; Robertson, J.; McErlean, C. S. P.; Wilson, C. Angew. Chem., Int. Ed. 2005, 44, 6157-6162
20. Fujiwara, K.; Yoshimoto, A.; Souma, S.-I.; Mishima, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 6819-6822
21. Sato, K.; Sasaki, M. Angew. Chem., Int. Ed. 2007, 46, 2518-2522
22. Park, J.; Kim, B.; Kim, H.; Kim, S.; Kim, D. Angew. Chem., Int. Ed. 2007, 46, 4726-4728
23. Sasaki, M.; Oyamada, K.; Takeda, K. J. Org. Chem. 2010, 75, 3941-3943
24. Lockwood, R. F.; Nicholas, K. M. Tetrahedron Lett. 1977, 4163-4167
25. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214
26. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1996, 108, 3128-3130
27. Green, J. R. Curr. Org. Chem. 2001, 5, 809-826
28. Teobald, B. J. Tetrahedron 2002, 58, 4133-4170
29. Diaz, D. D.; Betancort, J. M.; Martin, V. S. Synlett 2007, 343-359
30. Green, J. R. Eur. J. Org. Chem. 2008, 6053-6062
31. For the synthesis of cyclic ethers by intramolecular Nicholas reactions, see: Mukai, C.; Yamaguchi, S.; Sugimoto, Y.; Miyakoshi, N.; Kasamatsu, E.; Hanaoka, M. J. Org. Chem. 2000, 65, 6761-6765 and references cited therein
32. Crisóstomo, F. R. P.; Martín, T.; Martín, V. S. Org. Lett. 2004, 66, 565-568 and references cited therein
33. Hamajima, A.; Isobe, M. Org. Lett. 2006, 8, 1205-1208 and references cited therein
34. Hamajima, A.; Isobe, M. Angew. Chem., Int. Ed. 2009, 48, 2941-2945 and references cited therein
35. For a RCM with cobalt alkyne complex, see: Green, J. R. Synlett 2001, 353-356
36. Burlison, J. A.; Gray, J. M.; Young, D. G. J. Tetrahedron Lett. 2001, 42, 5363-5365
37. Young, D. G. J.; Burlison, J. A.; Peters, U. J. Org. Chem. 2003, 68, 3494-3497
38. Rosillo, M.; Casarrubios, L.; Domínguez, G.; Pérez- Castells, J. Org. Biomol. Chem. 2003, 1, 1450-1451
39. Yang, Z.-Q.; Geng, X.; Solit, D.; Pratilas, C. A.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 7881-7889
40. Ortega, N.; Martín, T.; Martín, V. S. Eur. J. Org. Chem. 2009, 554-563
41. Ortega, N.; Martín, T.; Martín, V. S. Org. Lett. 2006, 8, 871-873
42. The physical data are in agreement with the literature values: Darvesh, S.; Grant, A. S.; MaGee, D. I.; Valenta, Z. Can. J. Chem. 1991, 69, 712-722
43. The physical data are in agreement with the literature values: Emde, U.; Koert, U. Eur. J. Org. Chem. 2000, 1889-1904
44. The physical data are in agreement with the literature values: Janza, B.; Studer, A. J. Org. Chem. 2005, 70, 6991-6994
45. Diastereoisomers anti and syn of the α,α′-disubstituted linear ethers are defined as described below
46. For representative examples of enyne metathesis, see: Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382
47. 6-cycl'alkyne ethers, see: Liu, T.-Z.; Li, J.-M.; Isobe, M. Tetrahedron 2000, 56, 10209-10219
48. Betancort, J. M.; Martín, T.; Palazón, J. M.; Martín, V. S. J. Org. Chem. 2003, 68, 3216-3224
49. Crisóstomo, F. R. P.; Carrillo, R.; Martín, T.; Martín, V. S. Tetrahedron Lett. 2005, 46, 2829-2832
50. For previously reported syntheses of lauthisan, see: Tripathi, D.; Pandey, S. K.; Kumar, P. Tetrahedron 2009, 65, 2226-2231
51. Reference 7.
52. Miyakoshi, N.; Ohgaki, Y.; Masui, K.; Mukai, C. Heterocycles 2007, 74, 185-189
53. Reference 8.
54. Carreño, M. C.; Des Mazery, R.; Urbano, A.; Colobert, F.; Solladie, G. Org. Lett. 2005, 7, 2039-2042
55. Rhee, H. J.; Beom, H. Y.; Kim, H.-D. Tetrahedron Lett. 2004, 45, 8019-8022
56. Coster, M. J.; De Voss, J. J. Org. Lett. 2002, 4, 3047-3050
57. Suh, Y.-G.; Koo, B.-A.; Kim, E.-N.; Choi, N.-S. Tetrahedron Lett. 1995, 36, 2089-2092
58. Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792-793
59. Udding, J. H.; Giesselink, J. P. M.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1994, 59, 6671-6682
60. Carling, R. W.; Clark, J. S.; Holmes, A. B. J. Chem. Soc., Perkin Trans. 1 1992, 83-94
61. Paquette, L. A.; Sweeney, T. J. J. Org. Chem. 1990, 55, 1703-1704
62. Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Kim, B. H.; Ogilvie, W. W.; Yiannikouros, G.; Prasad, C. V. C.; Veale, C. A.; Hark, R. R. J. Am. Chem. Soc. 1990, 112, 6263-6276
63. Tsushima, K.; Murai, A. Chem. Lett. 1990, 761-764
64. Kotsuki, H.; Ushio, Y.; Kadota, I.; Ochi, M. J. Org. Chem. 1989, 54, 5153-5161
65. Carling, R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 565-567
66. Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron Lett. 1965' 6, 1091-1099
67. Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron 1968, 24, 4193-4205
68. Cameron, A. F.; Cheung, K. K.; Ferguson, G.; Robertson, J. M. J. Chem. Soc., Chem. Commun. 1965, 638
69. Cameron, A. F.; Cheung, K. K.; Ferguson, G.; Robertson, J. M. J. Chem. Soc. B 1969, 559-564
70. For a racemic total synthesis of laurencin, see: Murai, A.; Murase, H.; Matsue, H.; Masamune, T. Tetrahedron Lett. 1977, 18, 2507-2510 For asymmetric total syntheses of laurencin, see:
71. Adsool, V. A.; Pansare, S. V. Org. Biomol. Chem. 2008, 6, 2011-2015
72. Fujiwara, K.; Yoshimoto, S.; Takizawa, A.; Souma, S.; Mishima, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 6819-6822
73. Baek, S.; Jo, H.; Kim, H.; Kim, H.; Kim, S.; Kim, D. Org. Lett. 2005, 7, 75-77
74. Crimmins, M. T.; Emmitee, K. A. Org. Lett. 1999, 1, 2029-2032
75. Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660
76. Mújica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9729
77. Burton, J. W.; Clark, J. S.; Derrer, S.; Stork, T. C.; Bendall, J. G.; Holmes, A. B. J. Am. Chem. Soc. 1997, 119, 7483-7498
78. Krüger, J.; Hoffman, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504
79. Mújica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983-984
80. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966
81. Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348
82. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547
83. Jacobsen, E. N.; Markó, I.; Mungall, W. S.; Shröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968-1970
84. For a previous synthesis of the β-hydroxy-γ-lactone 28, see: Wang, Z. M.; Zhang, X. L.; Sharpless, K. B.; Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. Tetrahedron Lett. 1992, 33, 6407-6410 For synthesis of other β-hydroxy- γ -lactones using Sharpless asymmetric dihydroxylation, see:
85. García, C.; Martín, T.; Martín, V. S. J. Org. Chem. 2001, 66, 1420-1428
86. Martín, T.; Martín, V. S. Tetrahedron Lett. 2000, 41, 2503-2505
87. Harcken, C.; Brückner, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 2750-2752
88. Mulzer, J.; Schöllhorn, B. Angew. Chem., Int. Ed. Engl. 1990, 29, 431-432
89. Wuts, P. G. M.; Greene, T. W. Greenes Protective Groups in Organic Synthesis, 4th ed.; Wiley-VCH: New York, 2007.
90. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613
91. Crimmins and co-workers synthesized the protected homoallylic alcohol 27 (P = Bn) using asymmetric glycolate alkylation of an acyl oxazolidinone, see ref 20e.
92. Kim, S.; Kee, I. S. Tetrahedron Lett. 1990, 31, 2899-2900
93. Swern, D.; Mancuso, A. J.; Huang, S. J. Org. Chem. 1978, 43, 2480-2482
94. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486
95. Díaz, D. D.; Martín, V. S. Tetrahedron Lett. 2000, 41, 9993-9996
96. Sharpless, K. B.; Young, M. W. J. Org. Chem. 1974, 40, 947-949
97. Burke, S. D.; Voight, E. A. Org. Lett. 2001, 237-240