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Palladium-promoted cascade reactions of isonitriles and 6-iodo-N-propargylpyridones: Synthesis of mappicines, camptothecins, and homocamptothecins

Curran, DP and Du, W (2002) Palladium-promoted cascade reactions of isonitriles and 6-iodo-N-propargylpyridones: Synthesis of mappicines, camptothecins, and homocamptothecins. Organic Letters, 4 (19). 3215 - 3218. ISSN 1523-7060

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Abstract

Ambient-temperature reactions of electron-rich aryl isonitriles with substituted 6-iodo-N-propargylpyridones in the presence of silver carbonate and palladium acetate produce 11H-indolizino[1,2-b]quinolin-9-ones in good to excellent yield. Experimental evidence suggests that the process occurs though organopalladium rather than radical intermediates. It is applied to synthesis analogues of mappicine and camptothecin, including the silatecans DB-67 and DB-91 (homo-DB-67).


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Du, W
Date: 19 September 2002
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 4
Number: 19
Page Range: 3215 - 3218
DOI or Unique Handle: 10.1021/ol026408d
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Alkaloids--chemical synthesis; Camptothecin--analogs & derivatives; Camptothecin--chemical synthesis; Catalysis; Cross-Linking Reagents; Nitriles--chemistry; Palladium--chemistry
PubMed ID: 12227752
Date Deposited: 12 Feb 2014 22:56
Last Modified: 29 Jan 2019 15:55
URI: http://d-scholarship.pitt.edu/id/eprint/20489

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