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Volumn 44, Issue 43, 2003, Pages 7929-7932

Convergent synthesis of the F-K ring segment of brevetoxin B

Author keywords

Brevetoxin B; Convergent synthesis; Polycyclic ethers

Indexed keywords

ALPHA CHLOROACETOXY ETHER; BREVETOXIN; BREVETOXIN B; ETHER DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0141708680     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.003     Document Type: Article
Times cited : (9)

References (24)
  • 2
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    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6666-6675
    • Nicolaou, K.C.1    Duggan, M.E.2    Hwang, C.-K.3
  • 3
    • 0001737790 scopus 로고
    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6676-6682
    • Nicolaou, K.C.1    Duggan, M.E.2    Hwang, C.-K.3
  • 4
    • 0000136219 scopus 로고
    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6682-6690
    • Nicolaou, K.C.1    Hwang, C.-K.2    Duggan, M.E.3
  • 5
    • 0025150020 scopus 로고
    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (1990) Tetrahedron , vol.46 , pp. 4517-4552
    • Nicolaou, K.C.1    Nugiel, D.A.2    Couladouros, E.3    Hwang, C.-K.4
  • 6
    • 0034734601 scopus 로고    scopus 로고
    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7673-7676
    • Matsuo, G.1    Matsukura, H.2    Hori, N.3    Nakata, T.4
  • 7
    • 0034734652 scopus 로고    scopus 로고
    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7677-7680
    • Matsuo, G.1    Hori, N.2    Matsukura, H.3    Nakata, T.4
  • 8
    • 0034734614 scopus 로고    scopus 로고
    • For the synthetic studies of brevetoxin B, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6666-6675; (b) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682; (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690; (d) Nicolaou, K. C.; Nugiel, D. A.; Couladouros, E.; Hwang, C.-K. Tetrahedron 1990, 46, 4517-4552; (e) Matsuo, G.; Matsukura, H.; Hori, N.; Nakata, T. Tetrahedron Lett. 2000, 41, 7673-7676; (f) Matsuo, G.; Hori, N.; Matsukura, H.; Nakata, T. Tetrahedron Lett. 2000, 41, 7677-7680; (g) Matsukura, H.; Hori, N.; Matsuo, G.; Nakata, T. Tetrahedron Lett. 2000, 41, 7681-7684.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7681-7684
    • Matsukura, H.1    Hori, N.2    Matsuo, G.3    Nakata, T.4
  • 17
    • 85031060151 scopus 로고    scopus 로고
    • note
    • The Grignard reaction of the hydroxy aldehyde gave poor results.
  • 21
    • 0001268766 scopus 로고    scopus 로고
    • For the original conditions, see: (a) Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320; (b) Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191-198; (c) Kopecky, D. J.; Rychnovsky, S. D. Org. Synth. 2003, 80, 177-183.
    • (1996) J. Org. Chem. , vol.61 , pp. 8317-8320
    • Dahanukar, V.H.1    Rychnovsky, S.D.2
  • 22
    • 0033983302 scopus 로고    scopus 로고
    • For the original conditions, see: (a) Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320; (b) Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191-198; (c) Kopecky, D. J.; Rychnovsky, S. D. Org. Synth. 2003, 80, 177-18
    • (2000) J. Org. Chem. , vol.65 , pp. 191-198
    • Kopecky, D.J.1    Rychnovsky, S.D.2
  • 23
    • 85026864515 scopus 로고    scopus 로고
    • For the original conditions, see: (a) Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320; (b) Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191-198; (c) Kopecky, D. J.; Rychnovsky, S. D. Org. Synth. 2003, 80, 177-183.
    • (2003) Org. Synth. , vol.80 , pp. 177-183
    • Kopecky, D.J.1    Rychnovsky, S.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.