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Volumn 39, Issue 52, 1998, Pages 9633-9636

Concise synthesis of the bicyclic core of the chromoprotein antibiotics kedarcidin and neocarzinostatin by transannular reductive cyclization of a tetrayne precursor

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; KEDARCIDIN; ZINOSTATIN;

EID: 0032564554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02279-5     Document Type: Article
Times cited : (12)

References (22)
  • 2
    • 0001582792 scopus 로고
    • This work is remarkable not only for the transformation depicted, but also for the fact that, to the best of our knowledge, it describes the earliest example of a biradical-forming electrocyclization reaction
    • 2. Mayer, J.; Sondheimer, F. J. Am. Chem. Soc. 1966, 88, 602, 603. This work is remarkable not only for the transformation depicted, but also for the fact that, to the best of our knowledge, it describes the earliest example of a biradical-forming electrocyclization reaction.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 602
    • Mayer, J.1    Sondheimer, F.2
  • 7
    • 0010329829 scopus 로고    scopus 로고
    • note
    • 6. It was crucial to the success of these transformations that the temperature of the Swern oxidation be maintained at -78 °C and that methanol be added to the dibromoolefination reaction in order to consume triphenylphosphine dibromide generated in situ. On scales <10 g, the bis-dibromoolefinated product was isolated in 65-79% yield; using 32 g of diol 3 the yield was 38%.
  • 8
    • 0010330639 scopus 로고    scopus 로고
    • note
    • 7. All new compounds afforded satisfactory spectroscopic and analytical data.
  • 12
    • 0010375907 scopus 로고    scopus 로고
    • note
    • 10. The structure shown is actually the enantiomer of 6, which was synthesized by an identical procedure, albeit starting with D-dimethyl tartrate.
  • 13
    • 0010376721 scopus 로고    scopus 로고
    • note
    • 11. By-products arising from over-desilylation were recovered and transformed to 6 by treatment with TIPSOTf and 2.6-lutidine in dichloromethane at 23 °C (mass recovery ∼ 96%).
  • 15
    • 0010375611 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum established that epoxidation of the olefin endocyclic to the 5-membered ring (rather than the 9-membered ring) had occurred.
  • 22
    • 0010330365 scopus 로고    scopus 로고
    • note
    • 17. The small amount of residual olefin 9 is believed to result from the quenching of a vinyl aluminate intermediate by hexamethyldisilazane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.