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Volumn 121, Issue 24, 1999, Pages 5653-5660

An asymmetric aldol - Ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin

Author keywords

[No Author keywords available]

Indexed keywords

LAURENCIN; UNCLASSIFIED DRUG;

EID: 0033597634     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990421k     Document Type: Article
Times cited : (209)

References (52)
  • 1
    • 33845374592 scopus 로고
    • Shimizu, Y.; Chou, H. N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chen. Soc. 1986, 108, 514-515. 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, 1144-1150. Shimizu, Y.; Bando, H.; Chou, H.-N.; Van Duyne, G.; Clardy, J. C. J. Chem. Soc., Chem. Commun. 1986, 1656-1658.
    • (1986) J. Am. Chen. Soc. , vol.108 , pp. 514-515
    • Shimizu, Y.1    Chou, H.N.2    Bando, H.3    Van Duyne, G.4    Clardy, J.C.5
  • 3
    • 37049081087 scopus 로고
    • Shimizu, Y.; Chou, H. N.; Bando, H.; Van Duyne, G.; Clardy, J. C. J. Am. Chen. Soc. 1986, 108, 514-515. 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, 1144-1150. Shimizu, Y.; Bando, H.; Chou, H.-N.; Van Duyne, G.; Clardy, J. C. J. Chem. Soc., Chem. Commun. 1986, 1656-1658.
    • (1986) J. Chem. Soc., Chem. Commun. , pp. 1656-1658
    • Shimizu, Y.1    Bando, H.2    Chou, H.-N.3    Van Duyne, G.4    Clardy, J.C.5
  • 5
    • 0001695256 scopus 로고
    • Murata, M.; Kumagai, M.; Lee, J. S.; Yasumoto, T. Tetrahedron Lett. 1987, 28, 5869-5872. Takahashi, H.; Kusumi, T.; Kan, Y.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 7087-7090. Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929- 8931.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5869-5872
    • Murata, M.1    Kumagai, M.2    Lee, J.S.3    Yasumoto, T.4
  • 6
    • 0030599253 scopus 로고    scopus 로고
    • Murata, M.; Kumagai, M.; Lee, J. S.; Yasumoto, T. Tetrahedron Lett. 1987, 28, 5869-5872. Takahashi, H.; Kusumi, T.; Kan, Y.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 7087-7090. Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929- 8931.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7087-7090
    • Takahashi, H.1    Kusumi, T.2    Kan, Y.3    Satake, M.4    Yasumoto, T.5
  • 7
    • 0024815125 scopus 로고
    • Murata, M.; Kumagai, M.; Lee, J. S.; Yasumoto, T. Tetrahedron Lett. 1987, 28, 5869-5872. Takahashi, H.; Kusumi, T.; Kan, Y.; Satake, M.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 7087-7090. Murata, M.; Legrand, A. M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929-8931.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8929-8931
    • Murata, M.1    Legrand, A.M.2    Ishibashi, Y.3    Yasumoto, T.4
  • 12
    • 0008313164 scopus 로고
    • Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron 1968, 24, 4193-4205. Cameron, A. F.; Cheung, K. K.; Ferguson, G.; Monteath Robertson, J. J. Chem. Soc., Chem. Commun. 1965, 638.
    • (1968) Tetrahedron , vol.24 , pp. 4193-4205
    • Irie, T.1    Suzuki, M.2    Masamune, T.3
  • 18
    • 0032054664 scopus 로고    scopus 로고
    • Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113-158. Faulkner, D. J. Nat. Prod. Rep. 1997, 14, 259-302. Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75-125 and earlier reviews in the same series.
    • (1998) Nat. Prod. Rep. , vol.15 , pp. 113-158
    • Faulkner, D.J.1
  • 19
    • 0030841236 scopus 로고    scopus 로고
    • Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113-158. Faulkner, D. J. Nat. Prod. Rep. 1997, 14, 259-302. Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75-125 and earlier reviews in the same series.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 259-302
    • Faulkner, D.J.1
  • 20
    • 0030131103 scopus 로고    scopus 로고
    • and earlier reviews in the same series
    • Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113-158. Faulkner, D. J. Nat. Prod. Rep. 1997, 14, 259-302. Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75-125 and earlier reviews in the same series.
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 75-125
    • Faulkner, D.J.1
  • 22
    • 0026664095 scopus 로고
    • Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983-984. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4345-4348
    • Tsushima, K.1    Murai, A.2
  • 23
    • 0029006233 scopus 로고
    • Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983-984. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5958-5966
    • Bratz, M.1    Bullock, W.H.2    Overman, L.E.3    Takemoto, T.4
  • 24
    • 0002335268 scopus 로고    scopus 로고
    • Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983-984. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738.
    • (1996) Synlett , pp. 983-984
    • Mujica, M.T.1    Afonso, M.M.2    Galindo, A.3    Palenzuela, J.A.4
  • 25
    • 0040290459 scopus 로고    scopus 로고
    • Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983-984. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7499-7504
    • Krüger, J.1    Hoffmann, R.W.2
  • 26
    • 0032567409 scopus 로고    scopus 로고
    • Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. Synlett 1996, 983-984. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504. Mujica, M. T.; Afonso, M. M.; Galindo, A.; Palenzuela, J. A. J. Org. Chem. 1998, 63, 9728-9738.
    • (1998) J. Org. Chem. , vol.63 , pp. 9728-9738
    • Mujica, M.T.1    Afonso, M.M.2    Galindo, A.3    Palenzuela, J.A.4
  • 27
    • 85022720403 scopus 로고
    • Attaur-Rahman, A., Ed.; Elsevier Science Publishers: New York
    • For a review on the synthesis of medium-ring cyclic ethers, see: Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Attaur-Rahman, A., Ed.; Elsevier Science Publishers: New York 1992; Vol 10. For more recent examples, see: Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446-2452. Rychnovsky, S. D.; Dahanukar, V. H. J. Org. Chem. 1996, 61, 7648-7649. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256. Nicolaou, K. C.; Yang, Z.; Ouellette, M.; Shi, G.-Q.; Gärtner, P.; Gunzner, J. L.; Agrios, K. A.; Huber, R.; Chadha, R.; Huang, D. H. J. Am. Chem. Soc. 1997, 119, 8105-8106.
    • (1992) Studies in Natural Products Chemistry , vol.10
    • Moody, C.J.1    Davies, M.J.2
  • 28
    • 0030899135 scopus 로고    scopus 로고
    • For a review on the synthesis of medium-ring cyclic ethers, see: Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Attaur-Rahman, A., Ed.; Elsevier Science Publishers: New York 1992; Vol 10. For more recent examples, see: Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446-2452. Rychnovsky, S. D.; Dahanukar, V. H. J. Org. Chem. 1996, 61, 7648-7649. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256. Nicolaou, K. C.; Yang, Z.; Ouellette, M.; Shi, G.-Q.; Gärtner, P.; Gunzner, J. L.; Agrios, K. A.; Huber, R.; Chadha, R.; Huang, D. H. J. Am. Chem. Soc. 1997, 119, 8105-8106.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2446-2452
    • Berger, D.1    Overman, L.E.2    Renhowe, P.A.3
  • 29
    • 0029838260 scopus 로고    scopus 로고
    • For a review on the synthesis of medium-ring cyclic ethers, see: Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Attaur-Rahman, A., Ed.; Elsevier Science Publishers: New York 1992; Vol 10. For more recent examples, see: Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446-2452. Rychnovsky, S. D.; Dahanukar, V. H. J. Org. Chem. 1996, 61, 7648-7649. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256. Nicolaou, K. C.; Yang, Z.; Ouellette, M.; Shi, G.-Q.; Gärtner, P.; Gunzner, J. L.; Agrios, K. A.; Huber, R.; Chadha, R.; Huang, D. H. J. Am. Chem. Soc. 1997, 119, 8105-8106.
    • (1996) J. Org. Chem. , vol.61 , pp. 7648-7649
    • Rychnovsky, S.D.1    Dahanukar, V.H.2
  • 30
    • 33845279920 scopus 로고
    • For a review on the synthesis of medium-ring cyclic ethers, see: Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Attaur-Rahman, A., Ed.; Elsevier Science Publishers: New York 1992; Vol 10. For more recent examples, see: Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446-2452. Rychnovsky, S. D.; Dahanukar, V. H. J. Org. Chem. 1996, 61, 7648-7649. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256. Nicolaou, K. C.; Yang, Z.; Ouellette, M.; Shi, G.-Q.; Gärtner, P.; Gunzner, J. L.; Agrios, K. A.; Huber, R.; Chadha, R.; Huang, D. H. J. Am. Chem. Soc. 1997, 119, 8105-8106.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2248-2256
    • Overman, L.E.1    Thompson, A.S.2
  • 31
    • 0030821537 scopus 로고    scopus 로고
    • For a review on the synthesis of medium-ring cyclic ethers, see: Moody, C. J.; Davies, M. J. In Studies in Natural Products Chemistry; Attaur-Rahman, A., Ed.; Elsevier Science Publishers: New York 1992; Vol 10. For more recent examples, see: Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446-2452. Rychnovsky, S. D.; Dahanukar, V. H. J. Org. Chem. 1996, 61, 7648-7649. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256. Nicolaou, K. C.; Yang, Z.; Ouellette, M.; Shi, G.-Q.; Gärtner, P.; Gunzner, J. L.; Agrios, K. A.; Huber, R.; Chadha, R.; Huang, D. H. J. Am. Chem. Soc. 1997, 119, 8105-8106.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8105-8106
    • Nicolaou, K.C.1    Yang, Z.2    Ouellette, M.3    Shi, G.-Q.4    Gärtner, P.5    Gunzner, J.L.6    Agrios, K.A.7    Huber, R.8    Chadha, R.9    Huang, D.H.10
  • 33
    • 0000081509 scopus 로고    scopus 로고
    • For a preliminary communication on the synthesis of medium-ring ethers by an asymmetric aldol-metathesis strategy, see: Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549.
    • (1997) J. Org. Chem. , vol.62 , pp. 7548-7549
    • Crimmins, M.T.1    Choy, A.L.2
  • 35
    • 0031031774 scopus 로고    scopus 로고
    • Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130. Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300. Clark, J. S.; Hamelin, O.; Hufton, R. Tetrahedron Lett. 1998, 39, 8321-8324.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 123-126
    • Clark, J.S.1    Kettle, J.G.2
  • 36
    • 0031023477 scopus 로고    scopus 로고
    • Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130. Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300. Clark, J. S.; Hamelin, O.; Hufton, R. Tetrahedron Lett. 1998, 39, 8321-8324.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 127-130
    • Clark, J.S.1    Kettle, J.G.2
  • 37
    • 0030753624 scopus 로고    scopus 로고
    • Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130. Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300. Clark, J. S.; Hamelin, O.; Hufton, R. Tetrahedron Lett. 1998, 39, 8321-8324.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6299-6300
    • Delgado, M.1    Martin, J.D.2
  • 38
    • 0032487811 scopus 로고    scopus 로고
    • Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130. Delgado, M.; Martin, J. D. Tetrahedron Lett. 1997, 38, 6299-6300. Clark, J. S.; Hamelin, O.; Hufton, R. Tetrahedron Lett. 1998, 39, 8321-8324.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8321-8324
    • Clark, J.S.1    Hamelin, O.2    Hufton, R.3
  • 42
    • 0345210072 scopus 로고
    • Kasahara, A.; Izumi, T.; Yanai, H. Chem. Ind. 1983, 898. Kritchevsky, D. J. Am. Chem. Soc. 1943, 65, 487. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836-9845.
    • (1983) Chem. Ind. , pp. 898
    • Kasahara, A.1    Izumi, T.2    Yanai, H.3
  • 43
    • 0003343672 scopus 로고
    • Kasahara, A.; Izumi, T.; Yanai, H. Chem. Ind. 1983, 898. Kritchevsky, D. J. Am. Chem. Soc. 1943, 65, 487. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836-9845.
    • (1943) J. Am. Chem. Soc. , vol.65 , pp. 487
    • Kritchevsky, D.1
  • 44
    • 0027067026 scopus 로고
    • Kasahara, A.; Izumi, T.; Yanai, H. Chem. Ind. 1983, 898. Kritchevsky, D. J. Am. Chem. Soc. 1943, 65, 487. Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836-9845.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9836-9845
    • Trost, B.M.1    Dumas, J.2    Villa, M.3
  • 48
    • 0345210071 scopus 로고    scopus 로고
    • note
    • Molecular mechanics calculations were made using the MM2 force field.


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