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  Total Synthesis and Structural Refinement of the Cyclic Tripyrrole Pigment Nonylprodigiosin

Fürstner, A., Grabowski, J., & Lehmann, C. W. (1999). Total Synthesis and Structural Refinement of the Cyclic Tripyrrole Pigment Nonylprodigiosin. The Journal of Organic Chemistry, 64(22), 8275-8280. doi:10.1021/jo991021i.

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Fürstner, Alois1, Author              
Grabowski, Jaroslaw1, Author              
Lehmann, Christian W.2, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Abstract: The first total synthesis of the cyclic prodigiosin derivative 4 is described, which constitutes a potential lead compound for the development of immunosuppressive agents. The key steps of this approach comprise a palladium-catalyzed Suzuki cross coupling reaction of the rather unstable pyrrole boronic acid derivative 17 with the electron rich pyrrolyl triflate 15 followed by a ring-closing metathesis reaction (RCM) of the resulting diene to form the macrocyclic ring of the target molecule. This transformation is best achieved by using the ruthenium indenylidene complex 21 as precatalyst. X-ray data of product 18·HCl thus formed suggest that the tautomeric form B properly describes the electron distribution within the heteroaromatic segment of this alkaloid, in which the central ring constitutes the azafulvene unit of the pyrrolylpyrromethene chromophore.

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Language(s): eng - English
 Dates: 1999-06-251999-10-01
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jo991021i
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 64 (22) Sequence Number: - Start / End Page: 8275 - 8280 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1