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Preparation of the tricyclic ketopyrrole core of roseophilin by radical macrocyclisation and Paal-Knorr condensation

Abstract:
A concise synthesis of the tricyclic ketopyrrole segment of roseophilin is described in which key features include stereoselective conjugate addition to monosubstituted cyclopentenones, optimised conditions for the rearrangement of l°-propargylic alcohols to vinyl ketones, 13-endo-trig free-radical macrocyclisation, and Paal-Knorr pyrrole condensation accompanied by oxidation in situ to complete the synthesis. Model studies on methylene oxidation α- to pyrrole rings are also described. © The Royal Society of Chemistry 2000.
Publication status:
Published

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Publisher copy:
10.1039/b005351l

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Hatley, RJD More by this author
Watkin, DJ More by this author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
20
Pages:
3389-3396
Publication date:
2000
DOI:
EISSN:
1364-5463
ISSN:
1470-4358
URN:
uuid:93f1b7ca-09d5-40ec-b8e8-bf58ae91db6a
Source identifiers:
37601
Local pid:
pubs:37601
Language:
English

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