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Solution phase synthesis of libraries of polycyclic natural product analogues by cascade radical annulation: Synthesis of a 64-member library of mappicine analogues and a 48-member library of mappicine ketone analogues

De Frutos, O and Curran, DP (2000) Solution phase synthesis of libraries of polycyclic natural product analogues by cascade radical annulation: Synthesis of a 64-member library of mappicine analogues and a 48-member library of mappicine ketone analogues. Journal of Combinatorial Chemistry, 2 (6). 639 - 649. ISSN 1520-4766

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Abstract

An improved cascade radical annulation route to (±)-mappicine, (S)-mappicine, and mappicine ketone is reported. The route is used to prepare libraries of mappicine and mappicine ketone analogues in a semiautomated fashion. Key diversity generating steps include the addition of an aldehyde to a Grignard reagent derived from a D-ring iodopyridine, N-propargylation of a subsequently derived iodopyridone, and cascade radical annulation with an isonitrile to form a mappicine analogue. Parallel oxidation of mappicine analogues produced mappicine ketones. The route is general and flexible and could be used to make very large libraries. It is also illustrative of how late stage cascade reactions can be employed strategically to generate libraries of polycyclic natural product analogues.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
De Frutos, O
Curran, DPcurran@pitt.eduCURRAN
Date: 1 January 2000
Date Type: Publication
Journal or Publication Title: Journal of Combinatorial Chemistry
Volume: 2
Number: 6
Page Range: 639 - 649
DOI or Unique Handle: 10.1021/cc000032i
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1520-4766
MeSH Headings: Alkaloids--chemistry; Biological Factors--chemistry; Combinatorial Chemistry Techniques; Ketones--chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry
PubMed ID: 11126292
Date Deposited: 14 Feb 2014 16:55
Last Modified: 23 Dec 2017 14:55
URI: http://d-scholarship.pitt.edu/id/eprint/20562

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