A two-step mimic for direct, asymmetric bromonium- and chloronium-induced polyene cyclizations

Tetrahedron

Volumn 66, Issue 26, 2010, Pages 4796-4804

  Snyder, Scott A ^a   Treitler, Daniel S ^a   Schall, Andreas ^a  

^a Columbia University ^*  (United States)

Author keywords

Halogenation; Polyene Cyclization; Total synthesis

Indexed keywords

4 ISOCYMOBARBATOL; BROMINE; CHLORINE; MERCURY DERIVATIVE; NATURAL PRODUCT; ORGANOMERCURY COMPOUND; POLYENE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOTRANSFORMATION; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 77954244311     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.037     Document Type: Article

References (95)

1. G. Stork, and A.W. Burgstahler J. Am. Chem. Soc. 77 1955 5068 5077
2. A. Eschenmoser, L. Ruzicka, O. Jeger, and D. Arigoni Helv. Chim. Acta 38 1955 1890 1904 For a recent perspective on this work fifty years after its original publication, see:
3. A. Eschenmoser, and D. Arigoni Helv. Chim. Acta 88 2005 3011 3050
4. For reviews, see:
5. J.K. Sutherland B.M. Trost, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 341 377
6. R.A. Yoder, and J.N. Johnston Chem. Rev. 105 2005 4730 4756 For a recent paper, including excellent references to the primary literature, see:
7. Y.-J. Zhao, and T.-P. Loh J. Am. Chem. Soc. 130 2008 10024 10029
8. For the isolation of the napyradiomycins, see:
9. K. Shiomi, H. Nakamura, H. Iinuma, H. Naganawa, T. Takeuchi, H. Umezawa, and Y. Iitaka J. Antibiot. 40 1987 1213 1219
10. K. Shiomi, H. Iinuma, M. Hamada, H. Naganawa, M. Manabe, C. Matsuki, T. Takeuchi, and H. Umezawa J. Antibiot. 39 1986 487 493
11. K. Shiomi, H. Nakamura, H. Iinuma, H. Naganawa, K. Isshiki, T. Takeuchi, H. Umezawa, and Y. Iitaka J. Antibiot. 39 1986 494 501
12. For a recent asymmetric total synthesis of napyradiomycin A1 (1), see:
13. S.A. Snyder, Z.-Y. Tang, and R. Gupta J. Am. Chem. Soc. 131 2009 5744 5745 For an earlier, racemic total synthesis, see:
14. K. Tatsuta, Y. Tanaka, M. Kojima, and H. Ikegami Chem. Lett. 2002 14 15
15. For work illustrating that both the snyderols and the napyradiomycins are prepared via vanadium-based haloperoxidases, see:
16. J.N. Carter-Franklin, and A. Butler J. Am. Chem. Soc. 126 2004 15060 15066
17. J.M. Winter, M.C. Moffitt, E. Zazopoulos, J.B. McAlpine, P.C. Dorrestein, and B.S. Moore J. Biol. Chem. 282 2007 16362 16368 For more recent references, see:
18. A. Butler, and S. Moriah Nature 460 2009 848 854
19. J.M. Winter, and B.S. Moore J. Biol. Chem. 284 2009 18577 18581
20. C. Wagner, M.E. Omari, and G. Koenig J. Nat. Prod. 72 2009 540 553
21. For reviews, see:
22. F.A. Vaillancourt, E. Yeh, D.A. Vosburg, S. Garneau-Tsodikova, and C.T. Walsh Chem. Rev. 106 2006 3364 3378
23. A. Butler, and J.V. Walker Chem. Rev. 93 1993 1937 1944
24. For selected examples, see:
25. E.E. van Tamelen, and E.J. Hessler J. Chem. Soc., Chem. Commun. 1966 411 413
26. L.E. Wolinsky, and D.J. Faulkner J. Org. Chem. 41 1976 597 600
27. T. Kato, I. Ichinose, A. Kamoshida, and Y. Kitahara J. Chem. Soc., Chem. Commun. 1976 518 519
28. A.G. González, J.D. Martín, C. Pérez, and M.A. Ramírez Tetrahedron Lett. 17 1976 137 138
29. T.R. Hoye, and M.J. Kurth J. Org. Chem. 43 1978 3693 3697
30. T. Kato, and I. Ichinose J. Chem. Soc., Perkin Trans. 1 1980 1051 1056
31. H.-M. Shieh, and G.D. Prestwich Tetrahedron Lett. 23 1982 4643 4646
32. T. Kato, M. Mochizuki, T. Hirano, S. Fujiwara, and T. Uyehara J. Chem. Soc., Chem. Commun. 1984 1077 1078
33. Y. Yamaguchi, T. Uyehara, and T. Kato Tetrahedron Lett. 26 1985 343 346
34. S. Fujiwara, K. Takeda, T. Uyehara, and T. Kato Chem. Lett. 1986 1763 1766
35. A. Tanaka, M. Sato, and K. Yamashita Agric. Biol. Chem. 54 1990 121 123
36. S.A. Snyder, and D.S. Treitler Angew. Chem., Int. Ed. 48 2009 7899 7903
37. For the isolation of 4, see:
38. E.G. Juagdan, R. Kalidindi, and P. Scheuer Tetrahedron 53 1997 521 528
39. D. Davyt, R. Fernandez, L. Suescun, A.W. Mombrú, J. Saldaña, L. Domínguez, J. Coll, M.T. Fujii, and E. Manta J. Nat. Prod. 64 2001 1552 1555 For the isolation of 5, see:
40. D.N. Young, B.M. Howard, and W. Fenical Tetrahedron Lett. 17 1976 41 44
41. For an excellent review on halogenated natural products, see: G.W. Gribble Acc. Chem. Res. 31 1998 141 152
42. A. Sakakura, A. Ukai, and K. Ishihara Nature 445 2007 900 903
43. E.P. White, and P.W. Robertson J. Chem. Soc. 1939 1509 1515
44. R.S. Brown Acc. Chem. Res. 30 1997 131 137
45. S.E. Denmark, M.T. Burk, and A.J. Hoover J. Am. Chem. Soc. 132 2010 1232 1233 For similar challenges in achieving the enantioselective addition of chalcogens such as sulfur onto alkenes, see:
46. S.E. Denmark, W.R. Collins, and M.D. Cullin J. Am. Chem. Soc. 131 2009 3490 3492
47. For some recent examples of the initial step, see:
48. K. Surendra, and E.J. Corey J. Am. Chem. Soc. 131 2009 13928 13929
49. K. Surendra, and E.J. Corey J. Am. Chem. Soc. 130 2008 8865 8869 For a classic example, see:
50. P.V. Fish, A.R. Sudhakar, and W.S. Johnson Tetrahedron Lett. 34 1993 7849 7852
51. For an example of such a cyclization of a bromohydrin precursor, see: E.A. Couladouros, and V.P. Vidali Chem. - Eur. J. 10 2004 3822 3835
52. C.A. Mullen, A.N. Campbell, and M.R. Gagné Angew. Chem., Int. Ed. 47 2008 6011 6014
53. J.H. Koh, and M.R. Gagné Angew. Chem., Int. Ed. 43 2004 3459 3461
54. For selected examples, see:
55. E.J. Corey, M.A. Tius, and J. Das J. Am. Chem. Soc. 102 1980 1742 1744
56. E.J. Corey, J.G. Reid, A.G. Myers, and R.W. Hahl J. Am. Chem. Soc. 109 1987 918 919
57. T.R. Hoye, A.J. Caruso, and M.J. Kurth J. Org. Chem. 46 1981 3550 3552
58. A.S. Gopalan, R. Prieto, B. Mueller, and D. Peters Tetrahedron Lett. 33 1992 1679 1682
59. H. Takao, A. Wakabayashi, K. Takahashi, H. Imagawa, T. Sugihara, and M. Nishizawa Tetrahedron Lett. 45 2004 1079 1082
60. M. Nishizawa, E. Morikuni, K. Asoh, Y. Kan, K. Uenoyama, and H. Imagawa Synlett 1995 169 170
61. R.V. Stevens, and K.F. Albizati J. Org. Chem. 50 1985 632 640
62. F.R. Jensen, and L.H. Gale J. Am. Chem. Soc. 81 1959 1261 1262
63. F.R. Jensen, and L.H. Gale J. Am. Chem. Soc. 82 1960 148 151
64. T.R. Hoye, and M.J. Kurth J. Org. Chem. 44 1979 3461 3467
65. Direct chlorine replacement with retention is, to the best of our knowledge, unknown in the primary literature. However, a few isolated examples, some with high control and others with little selectivity, are mentioned as unpublished results in the following monograph: F.R. Jensen, and B. Rickborn Electrophilic Substitution of Organomercurials 1968 McGraw Hill New York, NY pp 75-100
66. S.H. Kang, and M. Kim J. Am. Chem. Soc. 125 2003 4684 4685
67. S.H. Kang, M. Kim, and S.-Y. Kang Angew. Chem., Int. Ed. 43 2004 6177 6180
68. S.H. Kang, S.Y. Kang, C.M. Park, H.Y. Kwon, and M. Kim Pure Appl. Chem. 77 2005 1269 1276
69. R.M. Carlson, and A.H. Funk Tetrahedron Lett. 12 1971 3661 3664
70. T. Sugita, Y. Yamasaki, O. Itoh, and K. Ichikawa Bull. Chem. Soc. Jpn. 47 1974 1945 1947 Enantioselectivities in these cases were, at best, between 25 and 35%, though 5-15% was common for many substrates
71. 2O, and hexanes. In addition, the use of chiral ligands that decreased the electrophilicity of the metal center and thus led to the need for elevated reaction temperatures might also have been deleterious to enantiocontrol.
72. M. Nishizawa, H. Takenaka, H. Nishide, and Y. Hayashi Tetrahedron Lett. 24 1983 2581 2584
73. M. Nishizawa, H. Takenaka, and Y. Hayashi J. Org. Chem. 51 1986 806 813
74. These ligands were prepared primarily following the procedures of:
75. D.A. Evans, G.S. Peterson, J.S. Johnson, D.M. Barnes, K.R. Campos, and K.A. Woerpel J. Org. Chem. 63 1998 4541 4544
76. M. Bandini, P.G. Cozzi, M. Gazzano, and A. Umani-Ronchi Eur. J. Org. Chem. 2001 1937 1942
77. M. Glos, and O. Reiser Org. Lett. 2 2000 2045 2048
78. H. Werner, R. Vicha, A. Gissibl, and O. Reiser J. Org. Chem. 68 2003 10166 10168
79. For reviews on this ligand class, see:
80. H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151 4202
81. G. Desimoni, G. Faita, and K.A. Jørgensen Chem. Rev. 106 2006 3561 3651
82. J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325 335
83. Interestingly, if the mono-oxazoline version of the same ligand class was used, we achieved the opposite stereoselection with substrate 21 as indicated in the table below. Mono-oxazoline ligands have been used effectively in asymmetric reactions only on a few occasions: M. Yamauchi, T. Aoki, M.-Z. Li, and Y. Honda Tetrahedron: Asymmetry 12 2001 3133 3138
84. In all these studies, a reaction temperature of -78 °C was utilized; lower temperatures did not lead to improved enantioselectivity, though erosion was observed above -50 °C.
85. 2/bis-oxazoline complex to assist in our transition state model, but have been unsuccessful thus far in our efforts. For two simpler Hg(II)-based crystal structures, see:
86. J. Halfpenny, and R.W.H. Small Acta Crystallogr. C53 1997 438 443
87. D. Grdenic, Z. Popvic, M. Bruvo, and B. Korpar-Colig Inorg. Chim. Acta 190 1991 169 172
88. For the isolation of this natural product, see:
89. M.E. Wall, M.C. Wani, G. Manikumar, H. Taylor, T.J. Hughes, K. Gaetano, W.H. Gerwick, A.T. McPhail, and D.R. McPhail J. Nat. Prod. 52 1989 1092 1099
90. M.E. Wall J. Nat. Prod. 55 1992 1561 1568
91. For a previous total synthesis of this compound, see: A. Tanaka, and T. Oritani Biosci. Biotechnol. Biochem. 59 1995 516 517 Ref. 8 provides an improved synthesis
92. 2Hg are quite dangerous, higher molecular weight organomercurials are not anywhere near as toxic, and in fact are used in agrochemicals and medicine: H. Imagawa, T. Iyenaga, and M. Nishizawa Org. Lett. 7 2005 451 453 See also Ref. 20
93. For selected examples of carbon replacement, see:
94. P. Kocovsky J. Organomet. Chem. 687 2003 256 268
95. A.L. Tökés, G. Litkei, K. Gulácsi, S. Antus, E. Baits-Gács, C. Szántay, and L.L. Darkó Tetrahedron 55 1999 9283 9296