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Volumn 121, Issue 1, 1999, Pages 54-62

Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels - Alder reactions

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; HETEROCYCLIC COMPOUND; LAMELLARIN O; LUKIANOL A; NATURAL PRODUCT; NINGALIN A; PERMETHYLSTORNIAMIDE A; UNCLASSIFIED DRUG;

EID: 0033550480     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982078+     Document Type: Article
Times cited : (463)

References (49)
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    • Lukianol A and lamellarin O dimethyl ether: Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637. Lamellarin O and Q and lukianol A: Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207. Lamellarin K: Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259. Lamellarin D and H: Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951. Lamellarin G trimethyl ether: Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155.
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    • Lukianol A and lamellarin O dimethyl ether: Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637. Lamellarin O and Q and lukianol A: Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207. Lamellarin K: Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259. Lamellarin D and H: Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951. Lamellarin G trimethyl ether: Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155.
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    • Lukianol A and lamellarin O dimethyl ether: Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637. Lamellarin O and Q and lukianol A: Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207. Lamellarin K: Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259. Lamellarin D and H: Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951. Lamellarin G trimethyl ether: Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155.
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    • Lukianol A and lamellarin O dimethyl ether: Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637. Lamellarin O and Q and lukianol A: Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207. Lamellarin K: Banwell, M.; Flynn, B.; Hockless, D. Chem. Commun. 1997, 2259. Lamellarin D and H: Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951. Lamellarin G trimethyl ether: Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155.
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  • 30
    • 0345263077 scopus 로고    scopus 로고
    • note
    • 13C NMR (DMSO, 100 MHz) of our synthetic sample of 1 was identical in all respects except this additional broadened singlet was observed as a sharp singlet at δ 122.9, which we tentatively assign as C2.
  • 33
    • 0345263076 scopus 로고    scopus 로고
    • note
    • 2 requires 415.1698).
  • 39
    • 0344400223 scopus 로고    scopus 로고
    • note
    • Attempts at methyl ether cleavage under a variety of conditions with E,E-5 to provide 4 resulted in only partial methyl ether deprotection and subsequent decomposition.
  • 42
    • 0345694722 scopus 로고    scopus 로고
    • note
    • 12 requires 723.1166).
  • 43
    • 0344831698 scopus 로고    scopus 로고
    • note
    • 6, 400 MHz): δ 11.24 (br s, 1H), 7.18 (br s, 2H), 6.51 (s, 2H), 6.42 (s, 2H), 3.71 (s, 6H), 3.69 (s, 6H), 3.51 (s, 6H).
  • 45
    • 0345263075 scopus 로고    scopus 로고
    • note
    • We thank Professors Capon and Scheuer for providing copies of the original spectra of lamellarin O and lukianol A, respectively, for direct comparison.
  • 46
    • 0345263074 scopus 로고    scopus 로고
    • note
    • 9


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