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Volumn 75, Issue 1, 2003, Pages 1-17

Synthetic studies on the marine natural product halichondrins

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HALICHONDRIN B; LIGAND; NATURAL PRODUCT; NICKEL; SULFONAMIDE;

EID: 0037221227     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200375010001     Document Type: Conference Paper
Times cited : (74)

References (82)
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    • For isolation of the halichondrins from different species of sponges, see: (a) G. R. Pettit, C. L. Herald, M. R. Boyd, J. E. Leet, C. Dufresne, D. L. Doubek, J. M. Schmidt, R. L. Cerny, J. N. A. Hooper, K. C. Rutzler. J. Med. Chem. 34, 3339 (1991); G. R. Pettit, R. Tan, F. Gao, M. D. Williams, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. C. Chapuis, E. Hamel, R. Bai, J. N. A. Hooper, L. P. Tackett. J. Org. Chem. 58, 2538 (1993); (b) M. Litaudon, J. B. Hart, J. W. Blunt, R. J. Lake, M. H. G. Munro. Tetrahedron Lett. 35, 9435 (1994); M. Litaudon, S. J. H. Hickford, R. E. Lill, R. J. Lake, J. W. Blunt, M. H. G. Munro. J. Org. Chem. 62, 1868 (1997).
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    • Pettit, G.R.1    Tan, R.2    Gao, F.3    Williams, M.D.4    Doubek, D.L.5    Boyd, M.R.6    Schmidt, J.M.7    Chapuis, J.C.8    Hamel, E.9    Bai, R.10    Hooper, J.N.A.11    Tackett, L.P.12
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    • Litaudon, M.1    Hart, J.B.2    Blunt, J.W.3    Lake, R.J.4    Munro, M.H.G.5
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    • 0030966118 scopus 로고    scopus 로고
    • For isolation of the halichondrins from different species of sponges, see: (a) G. R. Pettit, C. L. Herald, M. R. Boyd, J. E. Leet, C. Dufresne, D. L. Doubek, J. M. Schmidt, R. L. Cerny, J. N. A. Hooper, K. C. Rutzler. J. Med. Chem. 34, 3339 (1991); G. R. Pettit, R. Tan, F. Gao, M. D. Williams, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. C. Chapuis, E. Hamel, R. Bai, J. N. A. Hooper, L. P. Tackett. J. Org. Chem. 58, 2538 (1993); (b) M. Litaudon, J. B. Hart, J. W. Blunt, R. J. Lake, M. H. G. Munro. Tetrahedron Lett. 35, 9435 (1994); M. Litaudon, S. J. H. Hickford, R. E. Lill, R. J. Lake, J. W. Blunt, M. H. G. Munro. J. Org. Chem. 62, 1868 (1997).
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    • Litaudon, M.1    Hickford, S.J.H.2    Lill, R.E.3    Lake, R.J.4    Blunt, J.W.5    Munro, M.H.G.6
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    • For recent reviews on Cr-mediated reactions, see: (a) A. Fürstner. Chem. Rev. 99, 991 (1999); (b) L. A. Wessjohann and G. Scheid. Synthesis 1 (1999); (c) N. A. Saccomano. Comprehensive Organic Synthesis, B. M. Trost and I. Fleming (Eds.), Vol. 1, p. 173, Pergamon, Oxford (1991).
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    • For recent reviews on Cr-mediated reactions, see: (a) A. Fürstner. Chem. Rev. 99, 991 (1999); (b) L. A. Wessjohann and G. Scheid. Synthesis 1 (1999); (c) N. A. Saccomano. Comprehensive Organic Synthesis, B. M. Trost and I. Fleming (Eds.), Vol. 1, p. 173, Pergamon, Oxford (1991).
    • (1999) Synthesis , pp. 1
    • Wessjohann, L.A.1    Scheid, G.2
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    • B. M. Trost and I. Fleming (Eds.), Pergamon, Oxford
    • For recent reviews on Cr-mediated reactions, see: (a) A. Fürstner. Chem. Rev. 99, 991 (1999); (b) L. A. Wessjohann and G. Scheid. Synthesis 1 (1999); (c) N. A. Saccomano. Comprehensive Organic Synthesis, B. M. Trost and I. Fleming (Eds.), Vol. 1, p. 173, Pergamon, Oxford (1991).
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    • For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
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    • and the references cited therein
    • For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
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    • Cooper, A.J.1    Pan, W.2    Salomon, R.G.3
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    • For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
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  • 28
    • 0037017780 scopus 로고    scopus 로고
    • and the references cited therein
    • For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
    • (2002) Tetrahedron , vol.58 , pp. 2011
    • Austad, B.C.1    Hart, A.C.2    Burke, S.D.3
  • 29
    • 85045568522 scopus 로고
    • For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
    • (1994) Synlett , pp. 38
    • Horita, K.1    Hachiya, S.2    Nagasawa, M.3    Hikota, M.4    Yonemitsu, O.5
  • 30
    • 0031722551 scopus 로고    scopus 로고
    • and references cited therein
    • For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
    • (1998) Chem. Pharm. Bull. , vol.46 , pp. 1199
    • Horita, K.1    Nagasawa, M.2    Sakurai, Y.3    Yonemitsu, O.4
  • 33
    • 85038462841 scopus 로고    scopus 로고
    • U.S. Patent 6214865, 6365759, and S/N 09/843,617, International Patent WO 99/65894 (pending)
    • (c) B. A. Littlefield, M. H. Palme, B. M. Seletsky, M. J. Towle, M. J. Yu, W. Zheng. U.S. Patent 6214865, 6365759, and S/N 09/843,617, International Patent WO 99/65894 (pending).
    • Littlefield, B.A.1    Palme, M.H.2    Seletsky, B.M.3    Towle, M.J.4    Yu, M.J.5    Zheng, W.6
  • 37
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    • note
    • 2Mg.
  • 38
    • 85038467421 scopus 로고    scopus 로고
    • note
    • 2 (96%).
  • 39
    • 85038461748 scopus 로고    scopus 로고
    • note
    • An additional benefit was later recognized for this protection; enolization was detected in the series with a MeO group at C31 but not in the series with a BnO group.
  • 53
    • 0033550177 scopus 로고    scopus 로고
    • and references cited therein
    • In cyclic systems, allylic and homoallylic alcohols are known to direct the stereochemical course in conjugate additions of Grignard and cuprate reagents. For example, see: F. F. Fleming, J. Guo, Q. Wang, D. Weaver, J. Org. Chem. 64, 8568 (1999) and references cited therein.
    • (1999) J. Org. Chem. , vol.64 , pp. 8568
    • Fleming, F.F.1    Guo, J.2    Wang, Q.3    Weaver, D.4
  • 55
    • 85038456551 scopus 로고    scopus 로고
    • note
    • 2C≡CH; (4) hydrostannylation, followed by iodination; and (5) trisylation.
  • 56
    • 0001567540 scopus 로고    scopus 로고
    • For asymmetric Cr-mediated allylation, see: (a) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 62, 2322 (1997); (b) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi. Angew. Chem. Int. Ed. 38, 3357 (1999) and M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Tetrahedron 57, 835 (2001).
    • (1997) J. Org. Chem. , vol.62 , pp. 2322
    • Sugimoto, K.1    Aoyagi, S.2    Kibayashi, C.3
  • 57
    • 0033571364 scopus 로고    scopus 로고
    • For asymmetric Cr-mediated allylation, see: (a) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 62, 2322 (1997); (b) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi. Angew. Chem. Int. Ed. 38, 3357 (1999) and M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Tetrahedron 57, 835 (2001).
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3357
    • Bandini, M.1    Cozzi, P.G.2    Melchiorre, P.3    Umani-Ronchi, A.4
  • 58
    • 0035961114 scopus 로고    scopus 로고
    • For asymmetric Cr-mediated allylation, see: (a) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 62, 2322 (1997); (b) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi. Angew. Chem. Int. Ed. 38, 3357 (1999) and M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Tetrahedron 57, 835 (2001).
    • (2001) Tetrahedron , vol.57 , pp. 835
    • Bandini, M.1    Cozzi, P.G.2    Umani-Ronchi, A.3
  • 60
    • 85038461945 scopus 로고    scopus 로고
    • note
    • 3NCl/THF, and (3) NaH/1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) or 1,1,3,3-tetramethylurea (TMU), were routinely used to screen a ligand. The ratios given in Scheme 8 were obtained under condition 1, whereas those given in Scheme 7 were obtained under condition 3.
  • 64
    • 85038456739 scopus 로고    scopus 로고
    • note
    • 3Al/toluene/-5 °/1 h, RT/14 h, and then -20 °C/1 D for 38.
  • 65
    • 0035913709 scopus 로고    scopus 로고
    • A four-centered transition state involving one vinylchromium species was suggested for an intramolecular Ni(II)/Cr(II)-mediated coupling: D. W. C. MacMillan, L. E. Overman, L. D. Pennington. J. Am. Chem. Soc. 123, 9033 (2001) and 117, 10391 (1995).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9033
    • MacMillan, D.W.C.1    Overman, L.E.2    Pennington, L.D.3
  • 66
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    • A four-centered transition state involving one vinylchromium species was suggested for an intramolecular Ni(II)/Cr(II)-mediated coupling: D. W. C. MacMillan, L. E. Overman, L. D. Pennington. J. Am. Chem. Soc. 123, 9033 (2001) and 117, 10391 (1995).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10391
  • 75
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    • note
    • The rate of coupling was found significantly faster in MeCN than in EtCN. However, the enantioselectivity was significantly lower in MeCN than in EtCN.
  • 77
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    • note
    • 2 in several portions (3∼4 x 1 mol %), the homocoupling of 28 could be avoided.
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    • (b) Y. Okude, T. Hiyama, H. Nozaki. Tetrahedron Lett. 43, 3829 (1977); M. Kuroboshi, M. Tanaka, S. Kishimoto, H. Tanaka, S. Torii. Synlett. 69 (1999).
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    • Okude, Y.1    Hiyama, T.2    Nozaki, H.3
  • 82
    • 85038460182 scopus 로고    scopus 로고
    • note
    • 3, (2) montmorillonite clay/i-PrOH, (3) PPTS/i-PrOH, and (4) amberlite 15/i-PrOH.


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