Total synthesis of (-)-salicylihalamide

Chemistry - A European Journal

Volumn 7, Issue 24, 2001, Pages 5286-5298

  Fürstner, Alois ^a   Dierkes, Thorsten ^a   Thiel, Oliver R ^a   Blanda, Gaetano ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Cross coupling; Macrocycles; Metathesis; Natural products; Ruthenium

Indexed keywords

ESTERS; OLEFINS; PALLADIUM; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

MARINE NATURAL PRODUCTS;

HYDROGENATION;

3 IODOACRYLIC ACID; 4 METHOXY 7 [2 (4 METHOXYBENZYL)ETHYL] 9 METHOXYMETHYL 10 METHYL 7,8,9,10,11,14 HEXAHYDRO 6 OXABENZOCYCLODODECEN 5 ONE; 4,7 DIMETHYL 3 OXOOCT 6 ENOIC ACID METHYL ESTER; 5 METHOXYMETHYL 6,9 DIMETHYL 3 OXODEC 8 ENOIC ACID TERT BUTYL ESTER; ACRYLIC ACID DERIVATIVE; ALKENE; ALKYNE DERIVATIVE; AMIDE; ANTINEOPLASTIC AGENT; BUTYNYLZINC CHLORIDE; CARBENOID; CHROMIUM CHLORIDE; COPPER; CYCLOALKENE; CYTOTOXIC AGENT; ESTER DERIVATIVE; FUSED HETEROCYCLIC RINGS; HEPT 2 EN 4 YNOIC CID METHYL ESTER; HEPTA 2,4 DIENOIC ACID METHYL ESTER; HYDROXYL GROUP; IMIDAZOL 2 YLIDENE; IMIDAZOLE DERIVATIVE; MACROLIDE; PALLADIUM; PHENOL; RUTHENIUM COMPLEX; SALICYLIHALAMIDE A; SALICYLIHALAMIDE B; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL IODIDE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DEAMINATION; DRUG SYNTHESIS; HYDROGENATION; SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; MOLECULAR STRUCTURE; SPECTRUM ANALYSIS;

EID: 0035905656     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO;2-G     Document Type: Article

References (105)

1. K. L. Erickson, J. A. Beutler, J. H. Cardellina, M. R. Boyd, J. Org. Chem. 1997, 62, 8188-8192.
2. It has recently been argued that salicylihalamide is not the metabolite of the sponge itself but likely the product of a microbial inhabitant thereof, cf. ref. [3].
3. M. R. Boyd, C. Farina, P. Belfiore, S. Gagliardi, J. W. Kim, Y. Hayakawa, J. A. Beutler, T. C. McKee, B. J. Bowman, E. J. Bowman, J. Pharmacol Exp. Ther. 2001, 297, 114-120.
4. J. W. Kim, K. Shin-ya, K. Furihata, Y. Hayakawa, H. Seto, J. Org. Chem. 1999, 64, 153-155.
5. R. Jansen, B. Kunze, H. Reichenbach, G. Höfle, Eur. J. Org. Chem. 2000, 913-919.
6. T. C. McKee, D. L. Galinis, L. K. Pannell, J. H. Cardellina, J. Laakso, C. M. Ireland, L. Murray, R. J. Capon, M. R. Boyd, J. Org. Chem. 1998, 63, 7805-7810.
7. K. A. Dekker, R. J. Aiello, H. Hirai, T. Inagaki, T. Sakakibara, Y. Suzuki, J. F. Thompson, Y. Yamauchi, N. Kojima, J. Antibiot. 1998, 51, 14-20.
8. a) A. Fürstner, G. Seidel, N. Kindler, Tetrahedron 1999, 55, 8215-8230;
9. b) A. Fürstner, N. Kindler, Tetrahedron Lett. 1996, 37, 7005-7008.
10. Total syntheses: a) Y. Wu, L. Esser, J. K. De Brabander, Angew. Chem. 2000, 112, 4478-4480;
11. Angew. Chem. Int. Ed. 2000, 39, 4308-4310;
12. b) D. Labrecque, S. Charron, R. Rej, C. Blais, S. Lamothe, Tetrahedron Lett. 2001, 42, 2645-2648;
13. c) B. B. Snider, F. Song, Org. Lett. 2001, 3, 1817-1820;
14. d) A. B. Smith, J. Zheng, Synlett 2001, 1019-1023.
15. A. Fürstner, O. R. Thiel, G. Blanda, Org. Lett. 2000, 2, 3731-3734.
16. Partial syntheses: a) G. I. Georg, Y. M. Ahn, B. Blackman, F. Farokhi, P. T. Flaherty, C. J. Mossman, S. Roy, K. L. Yang, Chem. Commun. 2001, 255-256;
17. b) Y. Wu, O. R. Seguil, J. K. De Brabander, Org. Lett. 2000, 2, 4241-4244;
18. c) A. Bhattacharjee, J. K. De Brabander, Tetrahedron Lett. 2000, 41, 8069-8073;
19. d) for a comparison of the RCM and macrolactonization strategy see: J. T. Feutrill, G. A. Holloway, F. Hilli, H. M. Hugel, M. A. Rizzacasa, Tetrahedron Lett. 2000, 41, 8569-8572.
20. See also the following corrigendum: K. L. Erickson, J. A. Beutler, J. H. Cardellina, M. R. Boyd, J. Org. Chem. 2001, 66, 1532.
21. For pertinent reviews see: a) T. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
22. b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
23. Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
24. c) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
25. d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144;
26. Angew. Chem. Int. Ed. Engl. 1997, 36, 2037-2056;
27. e) A. Fürstner, Top. Catal. 1997, 4, 285-299;
28. f) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388;
29. g) K. J. Ivin, J. Mol. Catal. A: Chem. 1998, 133, 1-16;
30. h) M. L. Randall, M. L. Snapper, J. Mol. Catal. A: Chem. 1998, 133, 29-40;
31. i) R. R. Schrock, Tetrahedron 1999, 55, 8141-8153;
32. j) M. E. Maier, Angew. Chem. 2000, 112, 2153-2157;
33. Angew. Chem. Int. Ed. 2000, 39, 2073-2077.
34. For methods allowing the formation of enamides see: a) B. B. Snider, F. Song, Org. Lett. 2000, 2, 407-408;
35. b) P. F. Hudrlik, A. M. Hudrlik, R. J. Rona, R. N. Misra, G. P. Withers, J. Am. Chem. Soc. 1977, 99, 1993-1996;
36. c) D. A. Alonso, E. Alonso, C. Nájera, M. Yus, Synlett 1997, 491-492;
37. d) T. Ogawa, T. Kiji, K. Hayami, H. Suzuki, Chem. Lett. 1991, 1443-1446;
38. e) I. Stefanuti, S.A. Smith, R. J. K. Taylor, Tetrahedron Lett. 2000, 41, 3735-3738;
39. f) B. M. Trost, J.-P. Surivet, Angew. Chem. 2001, 113, 1516-1519;
40. Angew. Chem. Int. Ed. 2001, 40, 1468-1471.
41. R. Shen, J. A. Porco, Jr., Org. Lett. 2000, 2, 1333-1336.
42. For comprehensive treatises, see: a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
43. b) T. Ohkuma, R. Noyori, in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 199-246.
44. A. Hadfield, H. Schweitzer, M. P. Trova, K. Green, Synth. Commun. 1994, 24, 1025-1028.
45. a) A. Fürstner, I. Konetzki, Tetrahedron 1996, 52, 15071-15078;
46. b) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072-3080;
47. c) A. Fürstner, K. Nikolakis, Liebigs Ann. 1996, 2107-2113.
48. Review: A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
49. A. Fürstner, G. Seidel, Synlett 1998, 161-162.
50. J. Mortier, J. Moyroud, B. Bennetau, P. A. Cain, J. Org. Chem. 1994, 59, 4042-4044.
51. For a discussion of this and other strategic goals in total synthesis see: A. Fürstner, Synlett 1999, 1523-1533.
52. D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739.
53. J. R. Gage, D. A. Evans, Org. Synth. 1990, 68, 83-91.
54. a) A. Devos, J. Remion, A.-M. Frisque-Hesbain, A. Colens, L. Ghosez, J. Chem. Soc. Chem. Commun. 1979, 1180;
55. b) B. Haveaux, A. Dekoker, M. Rens, A. R. Sidani, J. Toye, L. Ghosez, Org. Synth. 1980, 59, 26-34;
56. c) for a previous application in total synthesis see: A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817-2825.
57. a) M. W. Rathke, J. Deitch, Tetrahedron Lett. 1971, 2953-2956;
58. b) D. F. Taber, P. B. Deker, M. D. Gaul, J. Am. Chem. Soc. 1987, 109, 7488-7494.
59. a) D. F. Taber, L. J. Silverberg, Tetrahedron Lett. 1991, 32, 4227-4230;
60. b) T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa, S. Akutagawa, J. Chem. Soc. Chem. Commun. 1985, 922-924.
61. a) It should be pointed out, however, that concomitant reduction of the C=C double bond is avoided only if the alkene is tri-substituted; in contrast to the results reported in ref. [27a], a disubstituted alkene is not inert under the reaction conditions;
62. for similar experiences see: b) C. R. Harris, S. D. Kuduk, A. Balog, K. Savin, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 7050-7062;
63. c) S. L. Schreiber, S. E. Kelly, J. A. Porco, T. Sammakia, E. M. Suh, J. Am. Chem. Soc. 1988, 110, 6210-6218.
64. a) S. T. Nguyen, R. U. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1993, 115, 9858-9859;
65. b) S. T. Nguyen, L. K. Johnson, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1992, 114, 3974-3975;
66. c) P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110.
67. T. A. Kirkland, R. H. Grubbs, J. Org. Chem. 1997, 62, 7310-7318.
68. Review: O. Mitsunobu, Synthesis 1981, 1-28.
69. a) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250;
70. b) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Pedersen, J. Am. Chem. Soc. 1999, 121, 2674-2678;
71. c) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790;
72. d) T. Weskamp, F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann, Angew. Chem. 1999, 111, 2573-2576;
73. Angew. Chem. Int. Ed. 1999, 38, 2416-2419;
74. e) A. Fürstner, O. R. Thiel, L. Ackermann, H.-J. Schanz, S. P. Nolan, J. Org. Chem. 2000, 65, 2204-2207;
75. f) A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236-3253.
76. It is essential to quench the reaction mixture by addition of ethyl vinyl ether in order to inactivate the catalyst prior to work-up.
77. C. W. Lee, R. H. Grubbs, Org. Lett. 2000, 2, 2145-2147.
78. a) A. Fürstner, O. R. Thiel, N. Kindler, D. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995;
79. b) A. Fürstner, O. R. Thiel, L. Ackermann, Org. Lett. 2001, 3, 449-451.
80. For a discussion of how chelation effects RCM see: a) A. Fürstner, Top. Organomet. Chem. 1998, 1, 37-72;
81. b) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136.
82. For a pertinent review on the control of conformational space of acyclic compounds see: R. W. Hoffmann, Angew. Chem. 2000, 112, 2134-2150;
83. Angew. Chem. Int. Ed. 2000, 39, 2054-2070, and references therein.
84. For previous examples showing the influence of remote substituents on the stereochemical outcome of RCM, see for example: a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943;
85. b) A. Fürstner, K. Langemann, Synthesis 1997, 792-803;
86. c) D. Meng, D.-S. Su, A. Balog, P. Bertinato, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zeng, T.-C. Chou, L. He, S. B. Horwitz, J. Am. Chem. Soc. 1997, 119, 2733-2734;
87. d) it should be pointed out that the changed stereochemical course during the cyclization of the O-protected diene 25c versus that of the O-unprotected substrates 25a, b does not reflect an increased thermodynamic stability of the corresponding (E)-cycloalkene 26c relative to its (Z)-isomer. Semiempirical calculations (MNDO(AM1)) indicate that in both cases the corresponding (E)-alkenes are thermodynamically slightly more stable. We thank Dr. K. Angermund for carrying out these calculations.
88. W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett. 1989, 30, 5603-5606.
89. For precedence see: a) A. I. McDonald, L. E. Overman, J. Org. Chem. 1999, 64, 1520-1528;
90. b) L. A. Paquette, I. Collado, M. Purdie, J. Am. Chem. Soc. 1998, 120, 2553-2562.
91. a) G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748-2749;
92. b) S. Zhang, D. Zhang, L. S. Liebeskind, J. Org. Chem. 1997, 62, 2312-2313.
93. Note that the (Z,Z)-configurated amide 42 is rather labile and that in the paper of Porco et al. (ref. [15]) only E,E-configurated dienoic acid amides have been cross coupled.
94. S. Ma, X. Lu, Z. Li, J. Org. Chem. 1992, 57, 709-713.
95. E.-I. Negishi, F. Liu, in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 1-47.
96. a) Y. Oikawa, T. Yoshioka, O. Yonemitsu, Tetrahedron Lett. 1982, 23, 885-888;
97. b) A. Fürstner, K. Radkowski, J. Grabowski, C. Wirtz, R. Mynott, J. Org. Chem. 2000, 65, 8758-8762.
98. a) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549-7552;
99. b) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
100. a) K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408-7410;
101. b) A. Fürstner, Chem. Rev. 1999, 99, 991-1045.
102. For an optimization of the solvent system for Takai olefination reactions see: D. A. Evans, W. C. Black, J. Am. Chem. Soc. 1993, 115, 4497-4513.
103. a) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317;
104. b) A. Fürstner, C. Mathes, K. Grela, Chem. Commun. 2001, 1057-1059.
105. Phenolate complexes of Ru are known to be catalytically active in RCM reactions, see: S. Chang, L. Jones, C. Wang, L. M. Henling, R. H. Grubbs, Organometallics 1998, 17, 3460-3465.