Total synthesis of (-)-amphidinolide P

Organic Letters

Volumn 2, Issue 7, 2000, Pages 945-948

  Williams, David R ^a   Myers, Brian J ^a   Mi, Liang ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE P; ANTINEOPLASTIC AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HETEROCYCLIC COMPOUND; MACROLIDE;

ANIMAL; ARTICLE; CHEMISTRY; DINOFLAGELLATE; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; DINOFLAGELLIDA; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; MACROLIDES;

EID: 0034611509     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0000197     Document Type: Article

References (52)

1. (a) For reviews on isolation of the amphidinolides, see: Kobayashi, J. In Comprehensive Natural Products Chemistry; Mori, K., Ed.; Elsevier: New York, 1999; Vol. 8, pp 619-634.
2. (b) Ishibashi, M.; Kobayashi, J. Heterocydes 1997, 44, 543-572.
3. Ishibashi, M.; Yamaguchi, N.; Sasaki, T.; Kobayashi, J. J. Chem. Soc., Chem. Commun. 1994, 1455-1456. Amphidinolide N displays antitumor potency (IC50 0.05 nM) at levels similar to those reported for the spongistatins.
4. Bauer, I.; Maranda, L.; Young, K. A.; Shimizu, Y.; Fairchild, C.; Cornell, L.; MacBeth, J.; Huang, S. J. Org. Chem. 1995, 60, 1084-1086. We postulate that caribenolide I is a metabolite, which may correspond to the cyclodehydration product arising from amphidinolide N (ref 2).
5. Matsunaga, K.; Nakatani, K.; Ishibashi, M.; Kobayashi, J.; Ohizumi, Y. Biochim. Biophys. Acta 1998, 1427, 24-32.
6. May, M. Environ. Health Perspect. 1998, 106, A284-A285.
7. (a) For synthetic studies directed toward the amphidinolides, see: Williams, D. R.; Meyer, K. G. Org. Lett. 1999. 1, 1303-1305.
8. (b) Ohi, K.; Nishiyama, S. Synlett 1999, 573-575.
9. (c) Terrell, L. R.; Ward, J. S., III; Maleczka, R. E., Jr. Tetrahedron Lett. 1999, 40, 3097-3100.
10. (d) Ishiyama, H.; Takemura, T.; Tsuda, M.; Kobayashi, J. J. Chem. Soc. Perkin Trans, 1 1999, 1163-1166.
11. (e) Eng, H. M.; Myles, D. C. Tetrahedron Lett. 1999, 40, 2275-2278.
12. (f) Chakraborty, T.; Thippeswamy, D. Synlett 1999, 150-152.
13. (g) Hollingworth, G. J.; Pattenden, G. Tetrahedron Lett. 1998, 39, 703-706.
14. (h) Chakraborty, T. K.; Das, S. Chem. Lett. 2000, 80-81.
15. Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198-11199.
16. Williams, D. R.; Meyer, K. G. Total Synthesis of (+)-Amphidinolide K. In Abstracts of Papers, 218th National Meeting of the American Chemical Society, 1999; American Chemical Society: Washington, DC, 1999; p 578-ORGN.
17. Ishibashi, M.; Takahashi, M.; Kobayashi, J. J. Org. Chem. 1995, 60, 6062-6066.
18. Epoxide 4 is available in a one-pot Sharpless epoxidation and protection sequence in 82% ee. See: Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
19. Khorana, H. G.; Goldberg, H. I.; Rammler, D. H.; Smith, M. J. Am. Chem. Soc. 1962, 84, 430-440.
20. Although DDQ has been used for removal of acetal and PMB ether protecting groups, removal of the MMTr protecting group using DDQ has not been previously utilized to the best of our knowledge. See: (a) Oku, A.; Kinugasa, M.; Kamada, T. Chem, Lett. 1993, 165-168.
21. (b) Tanemura, K.; Nishida, Y.; Suzuki, T.; Satsumabayashi. K.; Horaguchi, T. J. Chem. Res., Synop. 1999, 40-41.
22. (c) Tanemura, K.; Suzuki, T.; Horaguchi, T. Bull. Chem. Soc. Jpn. 1994, 67, 290-292.
23. (d) Paterson, I.; Cowden, C. J.; Rahn, V. S.; Woodrow, M. D. Synlett 1998, 915-917.
24. Mancuso, A. J.; Haung, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
25. Corey, E. J.; Fuchs, P. L. Tetrahedron Left. 1972, 3769-3772.
26. Zhang, H. X.; Gruibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
27. Epoxy alcohol 7 was prepared from 1,4-butyne diol in three steps (91% ee). See: Total Synthesis of (+)-Breynolide A. Jass, P. A. Ph.D. Thesis, Indiana University, 1994. Also see ref 10.
28. Nicolaou, K. C.; Duggan, M. E.; Ladduwahetty, T. Tetrahedron Lett. 1984, 25, 2069-2072.
29. Miller, R. B.; McGarvey, G. J. Org. Chem. 1979, 44, 4624-4633.
30. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7278.
31. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
32. (a) Sakurai, H.; Hosomi, A. Tetrahedron Lett. 1976, 16, 1295-1298.
33. (b) Hosomi, A.; Endo, M.; Sakurai, H. Chem. Lett. 1976, 941-942.
34. For the synthesis of the benzyl deravative of allylsilane 13, see: (a) Bunnelle, W. H.; Narayanan, B. A. Org. Synth. 1990, 69, 89-95
35. (b) Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2738-2741.
36. (c) Mickelson, T. J.; Koviach, J. L.; Forsyth, C. J. J. Org. Chem. 1996, 61, 9617-9620.
37. The absolute stereochemistry of 14 was determined by Mosher ester analysis. See: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
38. Mitsunobu, O. Synthesis 1981, 1.
39. See ref 21b for an example in which the Dess-Martin periodinane was used for a similar oxidation.
40. Sato, F.; Kusakabe, M.; Kato, T.; Kobayashi, Y. J. Chem. Soc., Chem. Commun. 1984, 1331-1332.
41. For reviews on the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 50.
42. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
43. (c) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780.
44. (d) Mitchell, T. N. Synthesis 1992, 803-815.
45. (a) This catalyst system was previously used for Stille coupling reactions of inflates by Baker, S. R.; Roth, G. P.; Sapino. C. Synth. Comm. 1990, 20, 2185-2189.
46. (b) For "ligandless" use of Palladium in various couplings, see: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551.
47. 3As in THF, but these conditions did not give any of the desired product for the coupling of 2 and 3 even under prolonged reaction times. For an example of a similar Stille coupling using a vinyl bromide, see: Romo, D.; Rzasa, R. M.; Shea, H. A.; Park, K.; Langenhan, J. M.; Sun, L.; Akhiezer, A.; Liu, J. O. J. Am. Chem. Soc. 1998, 120, 12237-12254.
48. (a) Mottet, C.; Hamelin, O.; Garavel, G.; Deprés, J.-P.; Greene, A. E. J. Org. Chem. 1999, 64, 1380-1382.
49. (b) Bader, A. R.; Cummings, L. O.; Vogel, H. A. J. Am. Chem. Soc. 1951, 73, 4195-4197.
50. (c) Bader, A. R.; Vogel, H. A. J. Am. Chem. Soc. 1952, 74, 3992-3994.
51. (a) Cambell, D. S.; Lawrie, C. W. J. Chem. Soc., Chem. Commun. 1971, 355.
52. (b) Witzeman, J. S. Tetrahedrom Lett. 1990, 31, 1401.