A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6463-6465

  Du, Yishu ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

CATALYSIS; METABOLISM; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

1,3 BUTADIENE; 2 BUTYNOATE; 3 METHYL 2 METHYLENECYCLOHEXANONE; CYCLOHEXANONE DERIVATIVE; HINESOL; NATURAL PRODUCT; PHOSPHINE; SPIROVETIVANE DERIVATIVE; TERT BUTYL 2,3 BUTADIENOATE; UNCLASSIFIED DRUG;

ARTICLE; BRAIN CIRCULATION; BRAIN METABOLISM; CATALYSIS; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS;

CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0043076391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034281f     Document Type: Article

References (43)

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20. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
21. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
22. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
23. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
24. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
25. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
26. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
27. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
28. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
29. For the synthesis of hinesol, see: (a) Marshall, J. A.; Brady, S. F. J. Org. Chem. 1970, 35, 4068. (b) Yamada, K.; Aoki, K.; Nagase, H.; Hayakawa, Y.; Hirata, Y. Tetrahedron Lett. 1973, 4967. (c) Büchi, G.; Berthet, D.; Decorzant, R.; Grieder, A.; Hauser, A. J. Org. Chem. 1976, 41, 3208. (d) Dauben, W. G.; Hart, D. J. J. Am. Chem. Soc. 1977, 99, 7307. (e) Chass, D. A.; Buddhasukh, D.; Magnus, P. D. J. Org. Chem. 1978, 43, 1750. (f) Ibuka, T.; Hayashi, K.; Minakata, H.; Ito, Y.; Inubushi, Y. Can. J. Chem. 1979, 57, 1579. (g) Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460. (h) Iwata, C.; Ida, Y.; Miyashita, K.; Nakanishi, T.; Yamada, M. Chem. Pharm. Bull. 1982, 30, 2738. (i) Murai, A.; Sato, S.; Masamune, T. Bull. Chem. Soc. Jpn. 1984, 57, 2276. (j) Paquette, L. A.; Yan, T.-H.; Wells, G. J. J. Org. Chem. 1984, 49, 3610. (k) Nyström, J.-E.; Helquist, P. J. Org. Chem. 1989, 54, 4695. (l) Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393. (m) Janake, S. N.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1997, 195. (n) Wang, J. J.; Yue, C. J.; Qiu, J.; Qian, C. Y. Chin. Chem. Lett. 1997, 8, 957. (o) Xie, P.; Chen, S. F.; Liang, X. T. Chin. Chem. Lett. 1998, 9, 353.
30. For the synthesis of the mixture of (+)-hinesol and (+)-10-epihinesol ((+)-hinesol is the mirror image of the natural isomer) see ref 10e.
31. (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
32. (b) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
33. Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901.
34. 3 (0.10 mmol, 10 mol %) in dry toluene (10 mL) was stirred at room temperature): total yield 63%; ratio of 6/7/8/9 94/6/0/0.
35. For a detailed mechanism of phosphine-catalyzed [3+2] cycloaddition, see ref 12b.
36. (a) Rezgui, F.; Gaied, M. M. E. Tetrahedron Lett. 1998, 39, 5965.
37. (b) Ishizaki, M.; Niimi, Y.; Hoshino, O. Chem. Lett. 2001, 546.
38. For the synthesis of -5 and the determination of its ee value, see: (a) Tamura, R.; Watabe, K.; Katayama, H.; Suzuki, H.; Yamamoto, Y. J. Org. Chem. 1990, 55, 408. (b) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895.
39. For the synthesis of -5 and the determination of its ee value, see: (a) Tamura, R.; Watabe, K.; Katayama, H.; Suzuki, H.; Yamamoto, Y. J. Org. Chem. 1990, 55, 408. (b) Tamura, R.; Watabe, K.; Ono, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 4895.
40. The ee value of (5S,6S)-6 was determined by HPLC analysis (column, CHIRALPAK AD) with 100:1 hexane:2-propanol as eluent.
41. Similar results were observed, see refs 10d and 10o.
42. Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579.
43. 2 (8.0 psi) as carrier gas.