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Volumn 64, Issue 14, 1999, Pages 5053-5061

Total synthesis of (±)-nisamycin

Author keywords

[No Author keywords available]

Indexed keywords

ALISAMYCIN; ANTIBIOTIC AGENT; ASUKAMYCIN; MANUMYCIN; NISAMYCIN; UNCLASSIFIED DRUG;

EID: 0033043416     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990413m     Document Type: Article
Times cited : (42)

References (55)
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    • For recent reviews on the chemistry of manumycin-type antibiotics, see: (a) Sattler, I.; Thiericke, R.; Zeeck, A. Nat. Prod. Rep. 1998, 15, 221. (b) Floss, H. G. Nat. Prod. Rep. 1997, 14, 433.
    • (1998) Nat. Prod. Rep. , vol.15 , pp. 221
    • Sattler, I.1    Thiericke, R.2    Zeeck, A.3
  • 12
    • 0031260232 scopus 로고    scopus 로고
    • For recent reviews on the chemistry of manumycin-type antibiotics, see: (a) Sattler, I.; Thiericke, R.; Zeeck, A. Nat. Prod. Rep. 1998, 15, 221. (b) Floss, H. G. Nat. Prod. Rep. 1997, 14, 433.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 433
    • Floss, H.G.1
  • 23
    • 0029925759 scopus 로고    scopus 로고
    • For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2101
    • Kapfer, I.1    Lewis, N.J.2    Macdonald, G.3    Taylor, R.J.K.4
  • 24
    • 0030565606 scopus 로고    scopus 로고
    • For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6619
    • Alcaraz, L.1    Macdonald, G.2    Kapfer, I.3    Lewis, N.J.4    Taylor, R.J.K.5
  • 25
    • 0029850984 scopus 로고    scopus 로고
    • For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
    • (1996) Chem. Commun. , pp. 2647
    • Macdonald, G.1    Lewis, N.J.2    Taylor, R.J.K.3
  • 26
    • 0032554776 scopus 로고    scopus 로고
    • For other syntheses of manumycin-type natural products, see: (a) Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101. (b) Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619. (c) Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Chem. Commun. 1996, 2647. (d) Alcaraz, L.; Taylor, R. J. K. Chem. Commun. 1998, 1157.
    • (1998) Chem. Commun. , pp. 1157
    • Alcaraz, L.1    Taylor, R.J.K.2
  • 27
    • 0001260043 scopus 로고    scopus 로고
    • In preliminary communications, we have reported the preparation of polyene side chains of manumycins using organozirconocene methodology: (a) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (b) Wipf, P.; Coish, P. D. G. Tetrahedron Lett. 1997, 38, 5073.
    • (1997) Pure Appl. Chem. , vol.69 , pp. 639
    • Wipf, P.1    Xu, W.2    Takahashi, H.3    Jahn, H.4    Coish, P.D.G.5
  • 28
    • 0030745359 scopus 로고    scopus 로고
    • In preliminary communications, we have reported the preparation of polyene side chains of manumycins using organozirconocene methodology: (a) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (b) Wipf, P.; Coish, P. D. G. Tetrahedron Lett. 1997, 38, 5073.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5073
    • Wipf, P.1    Coish, P.D.G.2
  • 35
    • 0345729480 scopus 로고    scopus 로고
    • note
    • 3) of an impure sample supported this assumption. Peak listings characteristic for the diketal: δ 3.13 (s, 6 H), 3.26 (s, 6 H), 4.54 (d, 2 H, J = 4.5 Hz), 5.19 (d, 1 H, J = 10.5 Hz), 5.23 (d, 1 H, J = 18 Hz), 5.75 (d, 1 H, J = 10.5 Hz), 5.8-6.0 (m, 1 H), 6.25 (dd, 1 H, J = 2.5, 10 Hz), 6.62 (br s, 1 H), 6.74 (br s, 1 H).
  • 36
    • 0345729483 scopus 로고    scopus 로고
    • note
    • Other epoxidation protocols, including enantioselective procedures, were inefficient.
  • 38
    • 0344434874 scopus 로고    scopus 로고
    • Unpublished results
    • Wipf, P.; Jeger, P. Unpublished results.
    • Wipf, P.1    Jeger, P.2
  • 40
    • 0033534602 scopus 로고
    • 1H NMR δ 1.00-1.45 (m, 21 H), 5.99 (d, 1 H, J = 15.0 Hz), 6.01 (dd, 1 H, J = 10.5, 15.0 Hz), 6.33 (dd, 1 H, J = 10.5, 14.5 Hz), 6.43 (dd, 1 H, J = 10.5, 15.0 Hz), 6.52-6.75 (m, 4 H), 6.84 (dd, 1 H, J = 7.5, 10.0 Hz), 7.10-7.48 (m, 3 H)). For a related cis-trans isomerization during tin-iodine exchange, see: Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1989, 64, 23.
    • (1989) J. Org. Chem. , vol.64 , pp. 23
    • Mapp, A.K.1    Heathcock, C.H.2
  • 41
    • 0344434876 scopus 로고    scopus 로고
    • note
    • 3-OD) δ 5.96 (d, 1 H, J = 15.0 Hz), 6.00 (d, 1 H, J = 13.0 Hz), 6.41 (dd, 1 H, J = 11.0, 15.0 Hz), 6.54 (dd, 1 H, J = 11.0, 15.0 Hz), 6.62-6.96 (m, 5 H), 7.12-7.40 (m, 3 H)).
  • 44
    • 0345297915 scopus 로고    scopus 로고
    • note
    • Treatment of the vinylstannane with NBS at low temperature resulted in partial conversion to the vinyl bromide. For example, stirring the stannane with 1 equiv of NBS at -40 °C for 1 h gave a 44% yield of the vinyl bromide 24 and a 34% yield of recovered starting material. However, conducting the experiment at higher temperature (0 °C) resulted in complete consumption of stannane. At this temperature, the vinyl bromide was obtained in 82% yield as a single stereoisomer (see Experimental Section).
  • 45
    • 0345297916 scopus 로고    scopus 로고
    • note
    • This compound was prepared in 51% yield by Horner-Emmons condensation of β-tributylstannyl acrolein with N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide (see the Experimental Section).
  • 47
    • 0345297917 scopus 로고    scopus 로고
    • note
    • This compound was prepared by Horner-Emmons condensation of β-tributylstannylacrolein with diethy(trimethylsilyloxycarbonyl-methy)phosphorane, followed by aqueous base workup and reprotection of the acid function using TIPS-Cl and imidazole (see the Experimental Section).


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