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Volumn 39, Issue 15, 2000, Pages 2732-2735

Synthesis of the kedarcidin core structure by a transannular cyclization pathway

Author keywords

Antibiotics; C C coupling; Cyclizations; Enediynes; Natural products

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; KEDARCIDIN;

EID: 0034604571     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2732::AID-ANIE2732>3.0.CO;2-9     Document Type: Article
Times cited : (58)

References (34)
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    • note
    • There is evidence that the kedarcidin chromophore is subject to nucleophilic activation as well. For example, it has been shown that 1 undergoes reduction/cycloaromatization with sodium borohydride: see: Ref. [1].
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    • Diyne 8 was prepared according to the protocol of Hirama for a closely related compound, differing from 8 only in the nature of the silyl protective groups: see: K.-i. Iida, M. Hirama, J. Am. Chem. Soc. 1994, 116, 10310-10311.
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    • For the use of (trimethylsilyl)diazomethyllithium in the alkynylation of aldehydes, see: K. Miwa, T. Aoyama, T. Shioiri, Synlett 1994, 107-108.
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    • The conversion of a diol to a cyclic sulfate is typically conducted in a two-step procedure, by cyclic sulfite formation, then sulfite oxidation (Y. Giao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538-7539). In the present case, decomposition occurred during oxidation of the diastereomeric cyclic sulfite intermediates. Sharpless and co-workers have shown that electron-deficient vicinal diols can be transformed into the corresponding cyclic sulfates directly, in one step, using sulfuryl chloride (K. P. M. Vanhessche, K. B. Sharpless, Chem. Eur. J. 1997, 3, 517-522). The conditions developed here were optimal for substrate 12 and differ significantly from those described by Sharpless and co- workers.
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    • The conversion of a diol to a cyclic sulfate is typically conducted in a two-step procedure, by cyclic sulfite formation, then sulfite oxidation (Y. Giao, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 7538-7539). In the present case, decomposition occurred during oxidation of the diastereomeric cyclic sulfite intermediates. Sharpless and co-workers have shown that electron-deficient vicinal diols can be transformed into the corresponding cyclic sulfates directly, in one step, using sulfuryl chloride (K. P. M. Vanhessche, K. B. Sharpless, Chem. Eur. J. 1997, 3, 517-522). The conditions developed here were optimal for substrate 12 and differ significantly from those described by Sharpless and co-workers.
    • (1997) Chem. Eur. J. , vol.3 , pp. 517-522
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    • note
    • When copper(1) acetate was used instead of copper(1) iodide compound 6 was still not formed, which may explain the failure of the comixing experiment.
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    • and references therein
    • Mechanisms involving single-electron transfer, although felt to be less likely, cannot be ruled out; see: W. F. Bailey, J. J. Patricia, J. Organomet. Chem. 1989, 352, 1-46, and references therein.
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    • note
    • +]: 548.1636; found: 548.1630.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.