Synthesis of Sub-units of Marine Polycyclic Ethers by Ring-closing Metathesis and Hydroboration of Enol Ethers

Tetrahedron

Volumn 55, Issue 27, 1999, Pages 8231-8248

  Clark, J Stephen ^a   Kettle, Jason G ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 DECENOL; 5 DECENYL ACETATE; 7 DODECENOL; 7 DODECENYL ACETATE; 9 TRICOSENE; ALKADIENE; DISPARLURE; PHEROMONE DERIVATIVE; SEX PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG OXIDATION; DRUG SYNTHESIS; INSECT; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033516686     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00303-8     Document Type: Article

References (51)

1. (a) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (b) Lee, M. S.; Repeta, D. J.; Nakanishi, K.; Zagorski, M. G. J. Am. Chem. Soc. 1986, 108, 7855.
2. (a) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (b) Lee, M. S.; Repeta, D. J.; Nakanishi, K.; Zagorski, M. G. J. Am. Chem. Soc. 1986, 108, 7855.
3. For a review of marine toxins, see: Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
4. (a) Shimizu, Y.; Chou, H.-N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514. (b) Pawlak, J.; Tempesta, M. S.; Golik. J.; Zagorski, M. G.; Lee, M. S.; Nakanishi, K.; Iwashita, T.; Gross, M. L.; Tomer, K. B. J. Am. Chem. Soc. 1987, 109, 1144.
5. (a) Shimizu, Y.; Chou, H.-N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 514. (b) Pawlak, J.; Tempesta, M. S.; Golik. J.; Zagorski, M. G.; Lee, M. S.; Nakanishi, K.; Iwashita, T.; Gross, M. L.; Tomer, K. B. J. Am. Chem. Soc. 1987, 109, 1144.
6. (a) Nukina, M.; Koyanagi, L. M.; Scheuer, P. J. Toxicon, 1984, 22, 169. (b) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (d) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; MacLeod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (e) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975.
7. (a) Nukina, M.; Koyanagi, L. M.; Scheuer, P. J. Toxicon, 1984, 22, 169. (b) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (d) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; MacLeod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (e) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975.
8. (a) Nukina, M.; Koyanagi, L. M.; Scheuer, P. J. Toxicon, 1984, 22, 169. (b) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (d) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; MacLeod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (e) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975.
9. (a) Nukina, M.; Koyanagi, L. M.; Scheuer, P. J. Toxicon, 1984, 22, 169. (b) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (d) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; MacLeod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (e) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975.
10. (a) Nukina, M.; Koyanagi, L. M.; Scheuer, P. J. Toxicon, 1984, 22, 169. (b) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929. (c) Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380. (d) Lewis, R. J.; Sellin, M.; Poli, M. A.; Norton, R. S.; MacLeod, J. K.; Sheil, M. M. Toxicon 1991, 29, 1115. (e) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975.
11. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361.
12. (a) Nagai, H.; Torigoe, K.; Satake, M.; Murata, M.; Yasumoto, T.; Hirota, H. J. Am. Chem. Soc. 1992, 114, 1102. (b) Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T.; J. Org. Chem. 1992, 57, 5448.
13. (a) Nagai, H.; Torigoe, K.; Satake, M.; Murata, M.; Yasumoto, T.; Hirota, H. J. Am. Chem. Soc. 1992, 114, 1102. (b) Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T.; J. Org. Chem. 1992, 57, 5448.
14. Murata, M.; Kumagai, M.; Lee, J. S.; Yasumoto, T. Tetrahedron Lett. 1987, 28, 5869.
15. Murata, M.; Naoki, H.; Iwashita, T.; Matsunaga, S.; Sasaki, M.; Yokoyama, A.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 2060.
16. For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330. (c) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (d) Zárraga, M.; Martín, J. D. Tetrahedron Lett. 1991, 32, 2249. (e) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
17. For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330. (c) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (d) Zárraga, M.; Martín, J. D. Tetrahedron Lett. 1991, 32, 2249. (e) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
18. For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330. (c) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (d) Zárraga, M.; Martín, J. D. Tetrahedron Lett. 1991, 32, 2249. (e) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
19. For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330. (c) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (d) Zárraga, M.; Martín, J. D. Tetrahedron Lett. 1991, 32, 2249. (e) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
20. For some examples of methods developed for the synthesis of polycyclic ether frameworks, see: (a) Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330. (c) Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040. (d) Zárraga, M.; Martín, J. D. Tetrahedron Lett. 1991, 32, 2249. (e) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
21. Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1996, 35, 589.
22. Nicolaou, K. C.; Yang, Z.; Shi, G.; Gunzner, J. L.; Agrios, K. A.; Gärtner, P. Nature 1998, 392, 264.
23. (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558. (b) Kadota, I.; Jung-Youl, P.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. (c) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.
24. (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558. (b) Kadota, I.; Jung-Youl, P.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. (c) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.
25. (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558. (b) Kadota, I.; Jung-Youl, P.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. (c) Morimoto, M.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 1996, 37, 6365.
26. For reviews of ring-closing metathesis and its application to synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371. (d) Grubbs, R. H.; Chang, S. Tetrahedron, 1998, 54, 4413.
27. For reviews of ring-closing metathesis and its application to synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371. (d) Grubbs, R. H.; Chang, S. Tetrahedron, 1998, 54, 4413.
28. For reviews of ring-closing metathesis and its application to synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371. (d) Grubbs, R. H.; Chang, S. Tetrahedron, 1998, 54, 4413.
29. For reviews of ring-closing metathesis and its application to synthesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1, 1998, 371. (d) Grubbs, R. H.; Chang, S. Tetrahedron, 1998, 54, 4413.
30. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
31. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
32. For a preliminary account of this work, see: Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123.
33. Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
34. Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565.
35. For examples of the hydroboration of related cyclic enol ethers, see: (a) Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc. 1990, 112, 3696. (b) Alvarez, E.; Rico, M.; Rodríguez, R. M.; Zurita, D.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3385. (c) Fei, F.; Murai, A. Synlett 1995, 863.
36. For examples of the hydroboration of related cyclic enol ethers, see: (a) Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc. 1990, 112, 3696. (b) Alvarez, E.; Rico, M.; Rodríguez, R. M.; Zurita, D.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3385. (c) Fei, F.; Murai, A. Synlett 1995, 863.
37. For examples of the hydroboration of related cyclic enol ethers, see: (a) Nicolaou, K. C.; McGarry, D. G.; Sommers, P. K. J. Am. Chem. Soc. 1990, 112, 3696. (b) Alvarez, E.; Rico, M.; Rodríguez, R. M.; Zurita, D.; Martín, J. D. Tetrahedron Lett. 1992, 33, 3385. (c) Fei, F.; Murai, A. Synlett 1995, 863.
38. Amouroux, R. Heterocycles 1984, 22, 1489.
39. 1-(t-Butyldimethylsilyloxy)-4-iodobutane was prepared from oxetane and 1-(t-butyldimethylsilyloxy)-5-iodopentane was prepared from tetrahydrofuran: Amouroux, R.; Jatcazk, M.; Chastrette, M. Bull. Soc. Chim. Fr. 1987, 505.
40. Watanabe, W. H.; Conlon, L. E. J. Am. Chem. Soc. 1957, 79, 2828.
41. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505.
42. Okazoe, T.; Takai, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1987, 52, 4410.
43. It is known that Lewis acids (including alkyl boranes) promote elimination of the intermediate organoboranes during the hydroboration of enol ethers: Pasto D. J.; Cumbo, C. C. J. Am. Chem. Soc. 1964, 86, 4343.
44. This finding is in accord with observations made by Grubbs, see ref. 17.
45. (a) Fu, G. C.; Grubbs, R. H.; J. Am. Chem. Soc. 1992, 114, 5426. (b) Fu, G. C.; Grubbs, R. H.; J. Am. Chem. Soc. 1993, 115, 3800.
46. (a) Fu, G. C.; Grubbs, R. H.; J. Am. Chem. Soc. 1992, 114, 5426. (b) Fu, G. C.; Grubbs, R. H.; J. Am. Chem. Soc. 1993, 115, 3800.
47. 4: 336.2301, found: 336.2302
48. The mixture of cyclo-dimers 20 was hydrogenated to give the saturated macrocyclic products, which were also characterised.
49. Alkene isomerisation to give an α,β-unsaturated ester has been observed during attempted ring-closing metathesis using a complex related to the catalyst 2: Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606.
50. For the synthesis of eight- and nine-membered cyclic ethers found in the brevetoxins and related natural products by ring-closing metathesis of atlylic ethers, see: Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127.
51. Joe, D.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8635.