Recent advances in the stereochemical determination and total synthesis of myxobacterial polyketides

Synlett

Volumn , Issue 20, 2010, Pages 2989-3007

  Kretschmer, Manuel ^a   Menche, Dirk ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

aldol reactions; macrocycles; polyketides; stereoselectivity; total synthesis

Indexed keywords

ARCHAZOLID A; ARCHAZOLID B; ETNANGIEN; MACROLIDE; POLYKETIDE; SPIRANGIEN; THUGGACIN; UNCLASSIFIED DRUG;

ALDOL REACTION; ARCHANGIUM GEPHYRA; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COUPLING FACTOR; CYSTOBACTER VIOLACEUS; ESTERIFICATION; HORNER WADSWORTH EMMONS REACTION; METHYLATION; MOLECULAR MODEL; MYXOCOCCALES; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SAPONIFICATION; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 78650178050     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259070     Document Type: Article

References (105)

1. For reviews, see:, Höfle G, Reichenbach H, In Sekundä rmetabolismus bei Mikroorganismen Kuhn W Fiedler H.-P Attempto Tübingen 1995 61-78
2. Reichenbach H, Höfle G, In Drug Discovery from Nature Grabley S Thierecke R Springer Berlin 1999 149-179
3. Williams D R., Org. Prep. Proced. Int. 2000 32 411
4. Wenzel S C., Müller R, Nat. Prod. Rep. 2007 24 1211
5. Nett M, König G, Nat. Prod. Rep. 2007 24 1245
6. Menche D, Nat. Prod. Rep. 2008 25 905
7. Weissman K J., Müller R, Bioorg. Med. Chem. 2009 17 2121
8. For a recent review, see:, Weissman K J., Müller R, Nat. Prod. Rep. 2010 27 1276
9. For an impressive total synthesis campaign by industry, see:, Klar U, Buchmann B, Schwede W, Skuballa W, Hoffmann J, Lichtner R B., Angew. Chem. Int. Ed. 2006 45 7942
10. Höfle G, Bedorf N, Steinmetz H, Schomburg D, Gerth K, Reichenbach H, Angew. Chem. Int. Ed. 1996 35 1567
11. Planar structure:, Höfle G, Reichenbach H, Sasse F, Steinmetz H, DE 4142951 C1 1993, Sasse F, Steinmetz H, Höfle G, Reichenbach H, J. Antibiot. 2003 56 520
12. Stereochemistry:, Hassfeld J, Farès C, Steinmetz H, Carlomagno T, Menche D, Org. Lett. 2006 8 4751
13. Relative configuration:, Niggemann J, Bedorf N, Flörke U, Steinmetz H, Gerth K, Reichenbach H, Höfle G, Eur. J. Org. Chem. 2005 5013
14. Absolute configuration by fragment synthesis:, Paterson I, Findlay A D., Anderson E A., Angew. Chem. Int. Ed. 2007 46 6699
15. Planar structure:, Jansen R, Irschik H, Reichenbach H, Höfle G, Liebigs Ann./Recl. 1997 1725
16. Stereochemistry
17. Janssen D, Albert D, Jansen R, Müller R, Kalesse M, Angew. Chem. Int. Ed. 2007 46 4898
18. Brodmann T, Janssen D, Kalesse M, J. Am. Chem. Soc. 2010 132 13610
19. Partial assignment of the relative configuration:, Steinmetz H, Irschik H, Kunze B, Reichenbach H, Höfle G, Jansen R, Chem. Eur. J. 2007 13 5822
20. Absolute and relative stereochemistry:, Bock M, Buntin K, Müller R, Kirschning A, Angew. Chem. Int. Ed. 2008 47 2308
21. Planar structure:, Höfle G, Reichenbach H, Irschik H, Schummer D, DE 19630980 B4 1998, Irschik H, Schummer D, Höfle G, Reichenbach H, Steinmetz H, Jansen R, J. Nat. Prod. 2007 70 1060
22. Stereochemistry:, Menche D, Arikan F, Perlova O, Horstmann N, Ahlbrecht W, Wenzel S C., Jansen R, Irschik H, Müller R, J. Am. Chem. Soc. 2008 130 14234
23. Rhizopodin was originally reported as a monomeric structure:, Höfle G, Reichenbach H, Sasse F, Steinmetz H, DE 4142950 A1 1993, Sasse F, Steinmetz H, Höfle G, Reichenbach H, J. Antibiot. 1993 46 741
24. Stereochemistry:, Horstmann N, Menche D, Chem. Commun. (Cambridge) 2008 5173
25. Hagelüken G, Albrecht G, Jansen R, Steinmetz H, Heinz D, Kalesse M, Sasse F, Schubert W D., Angew. Chem. Int. Ed. 2009 48 595
26. Another prominent example is the complex polyketide sorangicin for which initial stereochemical ambiguities at one of the stereogenic centers (C-10) were resolved by total synthesis:, Jansen R, Wray V, Irschik H, Reichenbach H, Höfle G, Tetrahedron Lett. 1985 26 6031
27. Smith A B., Dong S, Brenneman J B., Fox [nl]R J., J. Am. Chem. Soc. 2009 131 12109
28. Huss M, Sasse F, Kunze B, Jansen R, Steinmetz H, Ingenhorst G, Zeeck A, Wieczorek H, BMC Biochem. 2005 6 13
29. Bockelmann S, Menche D, Rudolph S, Bender T, Grond S, von Zezschwitz P, Muench S, Wieczorek H, Huss M, J. Biol. Chem. 2010 285 in press
30. For reviews, see:, Huss M, Wieczorek H, J. Exp. Biol. 2001 204 2597
31. Beyenbach K W., Wieczorek H, [nl]J. Exp. Biol. 2006 209 577
32. Huss M, Wieczorek H, [nl] J. Exp. Biol. 2009 212 341
33. Perez-Sayans M, Somoza-Martin J M., Barros-Angueira F, Rey J M. G., Cancer Treat. Rev. 2009 35 707
34. Menche D, Hassfeld J, Steinmetz H, Huss M, Wieczorek H, Sasse F, Eur. J. Org. Chem. 2007 1196
35. Menche D, Hassfeld J, Steinmetz H, Huss M, Wieczorek H, Sasse S, J. Antibiot. 2007 60 328
36. Matsumori N, Kaneno D, Murata M, Nakamura H, Tachibana K, J. Org. Chem. 1999 64 866
37. For recent reviews on the stereochemical determination of complex polyketides, see
38. Bifulco G, Dambruoso P, Gomez-Paloma L, Riccio R, Chem. Rev. 2007 107 3744
39. For a recent review on the determination of proton-carbon coupling constants, see:, Marquez B L., Gerwick W H., Williamson R T., Magn. Reson. Chem. 2001 39 499
40. Kozminski W, Nanz D, J. Magn. Reson. 2000 142 294
41. Mohamadi F, Richards N G. J., Guida W C., Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still W C., J. Comput. Chem. 1990 11 440
42. Still W C., Tempczyk A, Hawley R C., Hendrickson T, J. Am. Chem. Soc. 1990 112 6127
43. Farès C, Hassfeld J, Menche D, Carlomagno T, Angew. Chem. Int. Ed. 2008 47 3722
44. Menche D, Hassfeld J, Li J, Rudolph S, J. Am. Chem. Soc. 2007 129 6100
45. Menche D, Hassfeld J, Li J, Mayer K, Rudolph S, [nl] J. Org. Chem. 2009 74 7220
46. Roethle P A., Chen I T., Trauner D, J. Am. Chem. Soc. 2007 129 8960
47. For a review on archazolid syntheses, see:, von Zezschwitz P, Nachr. Chem. 2008 56 535
48. Huang Z H., Negishi E, J. Am. Chem. Soc. 2007 129 14788
49. ONeil G W., Black M J., Synlett 2010 107
50. Negishi E, Wang G, Rao H, Xu Z, J. Org. Chem. 2010 75 3151
51. Moulin E, Nevado C, Gagnepain J, Kelter G, Fiebig H.-H, Fürstner H, Tetrahedron 2010 66 6421
52. Brown H C., Bhat K S., Randad R S., J. Org. Chem. 1989 54 1570
53. Cowden C J., Paterson I, Org. React. (N. Y.) 1997 51 1
54. Still W C., Gennari C, Tetrahedron Lett. 1983 24 4405
55. Baker R, Castro J L., J. Chem. Soc., Perkin Trans. 1 1990 47
56. Inoue T, Liu J.-F, Buske D C., Abiko A, J. Org. Chem. 2002 67 5250
57. Li J, Li P, Menche D, Synlett 2009 2417
58. Corey E J., Helal C J., Angew. Chem. Int. Ed. 1998 37 1986
59. Kita Y, Maeda H, Omori K, Okuno T, Tamura Y, Synlett 1993 273
60. Hoye T R., Jeffrey C S., Tennakoon M A., Wang J, Zhao H J., J. Am. Chem. Soc. 2004 126 10210
61. Trost B M., Gunzner J L., J. Am. Chem. Soc. 2001 123 9449
62. Tanino K, Arakawa K, Satoh M, Iwata Y, Miyashita M, Tetrahedron Lett. 2006 47 861
63. Trost B M., Toste F D., Tetrahedron Lett. 1999 40 7739
64. For first SAR studies, see:, Menche D, Hassfeld J, Sasse F, Huss M, Wieczorek H, Bioorg. Med. Chem. Lett. 2007 17 1732
65. Darst S, Trends Biochem. Sci. 2004 29 159
66. Chopra I, Curr. Opin. Invest. Drugs 2007 8 600
67. Haebich D, von Nussbaum F, Angew. Chem. Int. Ed. 2009 48 3397
68. Mariani R, Maffioli S I., Curr. Med. Chem. 2009 16 430
69. Rychnovsky S D., Skalitzky D J., Tetrahedron Lett. 1990 31 945
70. Reid R, Piagentini M, Rodriguez E, Ashley G, Viswanathan N, Carney J, Santi D V., Hutchinson C R., McDaniel R, Biochemistry 2003 42 72
71. Caffrey P, ChemBioChem 2003 4 654
72. In a similar fashion, bioinformatic analyses were applied in the stereochemical determination of other myxobacterial polyketides; chivosazol: See also ref. 10 thuggacin: See also ref. 12
73. For a review on polypropanoate syntheses, see:, Li J, Menche D, Synthesis 2009 2293
74. Arikan F, Li J, Menche D, Org. Lett. 2008 10 3521
75. Li P, Li J, Arikan F, Ahlbrecht W, Dieckmann M, Menche D, J. Am. Chem. Soc. 2009 131 11678
76. Li P, Li J, Arikan F, Ahlbrecht W, Dieckmann M, Menche D, J. Org. Chem. 2010 75 2429
77. Li J, Menche D, Synthesis 2009 1904
78. Myers A G., Lanman B A., J. Am. Chem. Soc. 2002 124 12969
79. Tokunaga M, Larrow J F., Kakiuchi F, Jacobsen E N., Science (Washington, DC, U.S.) 1997 277 936
80. Evans D A., Chapman K T., Carriera E M., J. Am. Chem. Soc. 1988 110 3560
81. Menche D, Li P, Irschik H, Bioorg. Med. Chem. Lett. 2010 20 939
82. Bock M, Dehn R, Kirschning A, Angew. Chem. Int. Ed. 2008 47 9134
83. For a synthetic study towards thuggacin, see:, Tang S, Xu Z, Ye T, Tetrahedron: Asymmetry 2009 20 2027
84. Nagao Y, Hagiwara Y, Kumagai T, Ochichi M, J. Org. Chem. 1986 51 2391
85. Sakakura A, Kondo R, Umemura S, Ishihara K, Adv. Synth. Catal. 2007 349 1641
86. Nakagawa K, Konaka R, Nakata T, J. Org. Chem. 1963 27 1597
87. Evans D L., Minster D K., Jordis U, Hecht S M., Mazz A L., Meyers A I., J. Org. Chem. 1979 44 497
88. Tamao K, Akita M, Maeda K, Kumada M, J. Org. Chem. 1987 52 1100
89. Wipf P, Graham T H., J. Am. Chem. Soc. 2004 126 15346
90. Shiina I, Kubota M, Oshiumi H, Hashizume M, J. Org. Chem. 2004 69 1822
91. Frank B, Knauber J, Steinmetz H, Scharfe M, Blöcker H, Beyer S, Müller R, Chem. Biol. 2007 14 221
92. Paterson I, Findlay A D., Noti C, Chem. Commun. (Cambridge) 2008 6408
93. Paterson I, Findlay A D., Noti C, Chem. Asian J. 2009 4 594
94. Evans D A., Hoveyda A H., J. Am. Chem. Soc. 1990 112 6447
95. Paterson I, Channon J A., Tetrahedron Lett. 1992 33 797
96. Roush W R., Grover P T., Tetrahedron 1992 48 1981
97. Sorg A, Siegel K, Brückner R, Chem. Eur. J. 2005 11 1610
98. Lorenz M, Kalesse M, Tetrahedron Lett. 2007 48 2905
99. Lorenz M, Kalesse M, Org. Lett. 2008 10 4371
100. Evans D A., Clark J S., Metternich R, Novack V J., Sheppard G S., J. Am. Chem. Soc. 1990 112 866
101. Evans D A., Ennis D M., Le T, Mandel N, Mandel G, J. Am. Chem. Soc. 1984 106 1154
102. Evans D A., Trenkle W C., Zhang J, Burch J D., Org. Lett. 2005 7 3335
103. Paterson I, Lister M A., Tetrahedron Lett. 1988 29 585
104. Andringa H, Heus-Kloos Y A., Brandsma L, [nl]J. Organomet. Chem. 1987 336 C41
105. Lorenz M, Bluhm N, Kalesse M, Synthesis 2009 3061