Issue 20, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Jeremy Robertson,*a   Richard J. D. Hatleya  and  David J. Watkinb  

* Corresponding authors

a Dyson Perrins Laboratory, South Parks Road, Oxford, UK

b Chemical Crystallography Laboratory, 9 Parks Road, Oxford, UK

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 1°-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.

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Article information

DOI
https://doi.org/10.1039/B005351L
Article type
Paper
Submitted
04 Jul 2000
Accepted
17 Aug 2000
First published
02 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3389-3396

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

J. Robertson, R. J. D. Hatley and D. J. Watkin, J. Chem. Soc., Perkin Trans. 1, 2000, 3389 DOI: 10.1039/B005351L

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