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Volumn 40, Issue 9, 2001, Pages 1736-1739

Total synthesis of azinomycin A

Author keywords

Antitumor agents; Asymmetric synthesis; Natural products; Peptides; Total synthesis

Indexed keywords

ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL); TUMORS;

EID: 0035805308     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (88)

References (60)
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    • b) K. Yokoi, K. Nagaoka, T. Nakashima, Chem. Pharm. Bull. 1986, 34, 4554. Azinomycin B (2) is apparently identical to carzinophilin A, an antitumor agent isolated in 1954 from Streptomyces sahachiroi: T. Hata, F. Koga, Y. Sano, K. Kanamori, A. Matsumae, R. Sugawara, T. Hoshi, T. Shimi, S. Ito, S. Tomizawa, J. Antibiot. Ser. A 1954, 7, 107.
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    • Eds.: D. Barton, K. Nakanishi, O. Meth-Cohn, Pergamon
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    • R. S. Coleman, A. J. Carpenter, J. Org. Chem. 1993, 58, 4452. For the topic of "working models that do not work", see chapter 2 in: M. A. Sierra, M. C. de la Torre, Angew. Chem. 2000, 112, 1628-1650; Angew. Chem. Int. Ed. 2000, 39, 1538-1559.
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    • R. S. Coleman, A. J. Carpenter, J. Org. Chem. 1993, 58, 4452. For the topic of "working models that do not work", see chapter 2 in: M. A. Sierra, M. C. de la Torre, Angew. Chem. 2000, 112, 1628-1650; Angew. Chem. Int. Ed. 2000, 39, 1538-1559.
    • (2000) Angew. Chem. , vol.112 , pp. 1628-1650
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    • 0001758518 scopus 로고    scopus 로고
    • R. S. Coleman, A. J. Carpenter, J. Org. Chem. 1993, 58, 4452. For the topic of "working models that do not work", see chapter 2 in: M. A. Sierra, M. C. de la Torre, Angew. Chem. 2000, 112, 1628-1650; Angew. Chem. Int. Ed. 2000, 39, 1538-1559.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1538-1559
  • 51
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    • note
    • 12SiBr + Na: 946.2558).
  • 52
    • 85003737243 scopus 로고    scopus 로고
    • note
    • In a variety of model systems related to 20 and 1, the C13-H consistently resonates upfield in the (E)-isomer, whereas the N 16-H resonates downfield in this isomer: see ref. [13b].
  • 54
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    • L. Birkofer, E. Bierwirth, A. Ritter, Chem Ber. 1961, 94, 821. See also: M. Sakaitani, Y. Ohfune, J. Org. Chem. 1990, 55, 870.
    • (1990) J. Org. Chem. , vol.55 , pp. 870
    • Sakaitani, M.1    Ohfune, Y.2
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    • 85003560721 scopus 로고    scopus 로고
    • note
    • 10Si + Na: 732.2928).
  • 58
    • 85003736256 scopus 로고    scopus 로고
    • note
    • 10 + H: 596.2244).
  • 59
    • 85003610567 scopus 로고    scopus 로고
    • note
    • Model systems for the azabicyclic system of the natural products also exhibited instability when the C12-hydroxy protecting group was removed. In simple systems, deprotection of a trimethylsilyl ether was run in situ in an NMR tube because the product could not be isolated. For details, see ref. [11].
  • 60
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    • unpublished observations from this lab
    • R. J. Perez, unpublished observations from this lab.
    • Perez, R.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.