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Volumn 1, Issue 4, 1999, Pages 649-651

A formal total synthesis of roseophilin: Cyclopentannelation approach to the macrocyclic core

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; PYRROLE DERIVATIVE; ROSEOPHILIN;

EID: 0033606874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990124k     Document Type: Article
Times cited : (80)

References (32)
  • 10
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    • For reviews of the ring-closing metathesis reaction see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 11
    • 0002437895 scopus 로고    scopus 로고
    • Fürstner, A., Ed.; Springer-Verlag: Berlin, Heidelberg
    • (b) Nicolaou, K. C.; King, N. P.; He, Y. In Topics in Organometallic Chemistry; Fürstner, A., Ed.; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1, pp 73-104.
    • (1998) Topics in Organometallic Chemistry , vol.1 , pp. 73-104
    • Nicolaou, K.C.1    King, N.P.2    He, Y.3
  • 13
    • 0032507922 scopus 로고    scopus 로고
    • (b) Tius, M. A.; Busch-Petersen, J.; Yamashita, M. Tetrahedron Lett. 1998, 39, 4219-4222. For related work involving Nazarov cyclizations of allenyl ketones, see: Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4219-4222
    • Tius, M.A.1    Busch-Petersen, J.2    Yamashita, M.3
  • 14
    • 0032497668 scopus 로고    scopus 로고
    • (b) Tius, M. A.; Busch-Petersen, J.; Yamashita, M. Tetrahedron Lett. 1998, 39, 4219-4222. For related work involving Nazarov cyclizations of allenyl ketones, see: Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7491-7494
    • Hashmi, A.S.K.1    Bats, J.W.2    Choi, J.-H.3    Schwarz, L.4
  • 25
    • 0001537080 scopus 로고
    • For a review of acyl anion equivalents, see: Albright, J. D. Tetrahedron 1983, 39, 3207-3233.
    • (1983) Tetrahedron , vol.39 , pp. 3207-3233
    • Albright, J.D.1
  • 26
    • 0001070365 scopus 로고
    • Paquette, L. A., Ed.; John Wiley & Sons: New York
    • For a review of the Stetter reaction, see: Stetter, H.; Kuhlmann, H. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1991; Vol. 40, pp 407-496. See also: Stetter, H.; Haese, W. Chem. Ber. 1984, 117, 682-693.
    • (1991) Organic Reactions , vol.40 , pp. 407-496
    • Stetter, H.1    Kuhlmann, H.2
  • 27
    • 84984228620 scopus 로고
    • For a review of the Stetter reaction, see: Stetter, H.; Kuhlmann, H. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1991; Vol. 40, pp 407-496. See also: Stetter, H.; Haese, W. Chem. Ber. 1984, 117, 682-693.
    • (1984) Chem. Ber. , vol.117 , pp. 682-693
    • Stetter, H.1    Haese, W.2
  • 28
    • 0041572785 scopus 로고    scopus 로고
    • note
    • 6-Heptenal was prepared in 65% yield by reduction of commercially available 6-cyano-1-hexene with DIBAL.
  • 29
    • 0042073963 scopus 로고    scopus 로고
    • note
    • Stereochemistry was determined by NOE.
  • 30
    • 0042574986 scopus 로고    scopus 로고
    • note
    • 4 422.2457, found 422.2467.
  • 31
    • 0042574963 scopus 로고    scopus 로고
    • note
    • Ring-closing metathesis of the cis isomer of 2 proceeded in much lower yield (ca. 10%) under the same conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.