A formal total synthesis of pahnerolide A

Chemistry - A European Journal

Volumn 16, Issue 20, 2010, Pages 5858-5862

  Gowrisankar, Parthasarathy ^a   Pujari, Sandip A ^a   Kaliappan, Krishna P ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Antitumor agents; Julia Kocienski reaction; Metathesis; Natural products; Structure elucidation

Indexed keywords

ANTI-TUMOR AGENTS; KEY FEATURE; MACROCYCLES; MARINE NATURAL PRODUCTS; NATURAL PRODUCTS; PROTECTING GROUP; RING CLOSING METATHESIS; SHARPLESS EPOXIDATION; STRUCTURE ELUCIDATION; SYN-ALDOLS; TOTAL SYNTHESIS;

OLEFINS;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; MACROLIDE; PALLADIUM; PALMEROLIDE A;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CATALYSIS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 77952406295     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000428     Document Type: Article

References (80)

1. C.D. Amsler, K.B. Iken, J.B. McClintock, B.J. Baker in Marine Chemical Ecology (Eds.: J. B. McClintock. B. J. Baker). CRC Press, Boca Raton, 2001. pp. 267-300.
2. For more information on the Antarctic treaty, see: http://www.ats.aq/e/ ep.htm.
3. a) T. Diyabalange, C. D. Amsler, K. B. Iken, J. B. McClintock, B. J. Baker. J. Am. Chem. Soc. 2006, 128, 5630-5631:
4. b) M. D. Lebar, B.J. Baker. Tetrahedron Lett. 2007, 48, 8009-8010.
5. X. Jiang, B. Liu, S. Lebrelon, J. K. De Brabander, J. Am. Chem. Soc. 2007, 129, 6386-6387.
6. K. C. Nicolaou, R. Guduru. Y.-P. Sun. B. Banerji. D. Y.-K. Chen, Angew. Chem. 2007, 119, 6000-6004;
7. Angew. Chem. Int. Ed. 2007, 46, 5896-5900.
8. M. Penner, V. Rauniyar, L. T. Kaspar, D. G. Hall, J. Am. Chem. Soc. 2009, 131, 14216-14217.
9. a) K. P. Kaliappan, P. Gowrisankar, Synlett 2007, 1537-1540:
10. b) G. Canlagrel, C. Meyer. J. Cossy, Synlett 2007, 2983-2986;
11. S. Chandrasekhar. K. Vijeender, G. Chandrashekar, C. Raji Reddy, Tetrahedron: Asymmetry 2007, 18, 2473-2478;
12. J. Jägel. A. Schmauder, M. Binanzer, M. Maier, Tetrahedron 2007, 63, 13006-13017;
13. e) Formal synthesis: J. Jägel, M. Maier, Synthesis 2009, 2881-2892;
14. f) D. M. Jones, G. B. Dudley, Synlett 2010, 223-226.
15. a) K. C. Nicolaou, R. Guduru, Y.-P. Sun. B. Banerji, D. Y.-K. Chen, J. Am. Chem. Soc. 2008, 130, 3633-3644;
16. b) K. C. Nicolaou, G. Y. C. Leung, D. H. Dethe, R. Guduru. Y.-P. Sun. C. S. Lim, D. Y.-K. Chen. J. Am. Chem. Soc. 2008, 130, 10019-10023.
17. a) K. P. Kaliappan, P. Das, J. Org. Chem. 2009, 74, 6266-6274;
18. b) K. P. Kaliappan, D. Si, Synlett 2009, 2441-2444;
19. K. P. Kaliappan, V. Ravikumar, J. Org. Chem. 2007, 72, 6116-6126;
20. K. P. Kaliappan. V. Ravikumar, Synlett 2007, 0977-0980;
21. e) K. P. Kaliappan, A. V. Subrahmanyam, Org. Lett. 2007, 9, 1121-1124;
22. f) K. P. Kaliappan, R. S. Nandurdikar. M. M. Shaikh. Tetrahedron 2006, 62, 5064-5073:
23. g) K. P. Kaliappan. V. Ravikumar, S.A. Pujari. Tetrahedron Lett. 2006, 47, 981-984:
24. h) K. P. Kaliappan. R. S. Nandurdikar, Org. Biomol. Chem. 2005, 3, 3613-3614;
25. K. P. Kaliappan, N. Kumar, Tetrahedron 2005, 61, 7461-7469;
26. j) K. P. Kaliappan. V. Ravikumar, Org. Biomol. Chem. 2005, 3, 848-851;
27. k) K. P. Kaliappan. R. S. Nandurdikar. Chem. Commun. 2004, 2506-2507:
28. K. P. Kaliappan. N. Kumar, Tetrahedron Lett. 2003, 44, 379-381.
29. M. Oshima, H. Yamazaki, I. Shimizu, M. Nisar, J. Tsuji, J. Am. Chem. Soc. 1989, 111, 6280-6287.
30. a) P. J. Kocienski, B. Lythgoe, S. Ruston. J. Chem. Soc. Perkin Trans. 1 1978, 829-834:
31. b) P.J. Kocienski, B. Lythgoe. D. A. Roberts. J. Chem. Soc. Perkin Trans. 1 1978, 834-837;
32. P.J. Kocienski. B. Lythgoe, S. Ruston, J. Chem. Soc. Perkin Trans. 1 1979, 1290-1293:
33. P. J. Kocienski, B. Lythgoe, I. Walerhouse. J. Chem. Soc. Perkin Trans. 1 1980, 1045-1050;
34. e) P. R. Blakemore, W.J. Cole, P.J. Kocienski. A. Morley, Synlett 1998, 26-28:
35. f) P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563-2585.
36. J. Inanaga. K. Hirata. H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
37. For selected recent reviews on metathesis, see: a) A. Gradillas, J. Pèrez-Castells, Angew. Chem. 2006, 118, 6232-6247;
38. Angew. Chem. Int. Ed. 2006, 45, 6086-6101;
39. b) K. C. Nicolaou, P.G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601;
40. Angew. Chem. Int. Ed. 2005, 44, 4490-4527;
41. D.J. Wallace. Angew. Chem. 2005, 117, 1946-1949:
42. Angew. Chem. Int. Ed. 2005, 44, 1912-1915;
43. A. Giessert, S. T. Diver. Chem. Rev. 2004, 104, 1317-1382:
44. e) B. Schmidt. Eur. J. Org. Chem. 2004, 1865-1880:
45. f) A. H. Hoveyda, D. G. Gillingham, J. J. V. Veldhuizen. O. Kataoka. S. B. Garber, J. S. Kingsbury, J. P. Harrity, Org. Biomol. Chem. 2004, 2, 8-23:
46. g) R. H. Grubbs, Tetrahedron 2004, 60, 7117-7140;
47. h) J. Prunet, Angew. Chem. 2003, 115, 2932-2936:
48. Angew. Chem. Int. Ed. 2003, 42, 2826-2830:
49. Handbook of Metathesis, Vol.1-3 (Ed.: R. H. Grubbs). Wiley-VCH, Weinheim. 2003:
50. j) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
51. k) S. Kotha, N. Sreenivasachary, Indian J. Chem. 2001, 39, 763-780;
52. A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
53. Angew. Chem. Int. Ed. 2000, 39, 3012-3043:
54. R. Roy, S. Das. Chem. Commun. 2000, 519-529;
55. n) M. E. Maier, Angew. Chem. 2000, 112, 2153-2157;
56. Angew. Chem. Int. Ed. 2000, 39, 2073-2077;
57. o) L. Yet. Chem. Rev. 2000, 100, 2963-3007;
58. p) M. L. Randall. M. L. Snapper, Strem. Chem. 1998, 17, 1-9;
59. q) A.J. Phillips, A.D. Abell, Aldrichimica Acta 1999, 32, 75-85;
60. r) D. L. Wright, Curr. Org. Chem. 1999, 3, 211-240;
61. s) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388;
62. t) R. H. Grubbs. S. Chang. Tetrahedron 1998, 54, 4413-4450;
63. u) M. Schuster, S. Blechert. Angew. Chem. 1997, 109, 2124-2144;
64. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
65. J. Tan. M. A. Ciufolini, Org. Lett. 2006, 8, 4771-4774.
66. a) T. Katsuki. K. B. Sharpless. J. Am. Chem. Soc. 1980, 102, 5974-5976;
67. b) Z.-M. Wang, W.-S. Zhou, G.-Q. Lin. Tetrahedron Lett. 1985, 26, 6221-6224.
68. B. H. Lipshutz, D. Pallart, J. Monforte. H. Kotsuki. Tetrahedron Lett. 1985, 26, 705-708.
69. L. E. Overman, F. M. Knoll. Tetrahedron Lett. 1979, 20, 321-324.
70. S. Mann. S. Carillon, O. Breyne, A. Marquet. Chem. Eur. J. 2002, 8, 439-450.
71. R. Appel. Angew. Chem. 1975, 87, 863-874;
72. Angew. Chem. Int. Ed. Engl. 1975, 14, 801-811.
73. L. Alcaraz. J. J. Harnett. C. Mioskowski, J. P. Martel, T. Le Gall, D.S. Shin. J. R. Falck. Tetrahedron Lett. 1994, 35, 5449-5452.
74. Y. Gao, R. M. Hanson. J. M. Klunder, S. Y. Ko. H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
75. J. Mulzer, I, Böhm, J.-W. Bats, Tetrahedron Lett. 1998, 39, 9643-9646.
76. W.-R. Li, S.-Y. Han, M, M. Joullié, Tetrahedron 1993, 49, 785-802.
77. a) S. Hatakeyama, H. Irie, T. Shintani, Y. Noguchi, H. Yamada, M. Nishizawa, Tetrahedron 1994, 50, 13369-13376;
78. b) D. R. Williams, K. G. Meyer, J. Am. Chem. Soc. 2001, 123, 765-766.
79. K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408-7410.
80. S. S. Harried, C. P. Lee, G. Yang, T. I. H. Lee, D. C. Myles, J. Org. Chem. 2003, 68, 6646-6660.