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  Total Synthesis of Putative Chagosensine

Heinrich, M., Murphy, J. J., Ilg, M. K., Letort, A., Flasz, J., Philipps, P., et al. (2018). Total Synthesis of Putative Chagosensine. Angewandte Chemie International Edition, 57(41), 13575-13581. doi:10.1002/anie.201808937.

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 Creators:
Heinrich, Marc1, Author           
Murphy, John J.1, Author           
Ilg, Marina Kristina1, Author           
Letort, Aurélien1, Author           
Flasz, Jakub1, Author           
Philipps, Petra2, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: chloroalkenes; macrolides; organotin compounds; Stille coupling; total synthesis
 Abstract: The marine macrolide chagosensine is the only natural product known to date that embodies a Z,Z‐configured chloro‐1,3‐diene unit. This distinguishing substructure was prepared by a sequence of palladium‐catalyzed 1,2‐distannation of an alkyne precursor, regioselective Stille cross‐coupling at the terminus of the resulting bisstannyl alkene with an elaborated alkenyl iodide, followed by chloro‐destannation of the remaining internal site. The preparation of the required substrates centered on cobalt‐catalyzed oxidative cyclization reactions of hydroxylated olefin precursors, which allowed the 2,5‐trans‐disubstituted tetrahydrofuran rings, embedded into each building block, to be formed with excellent selectivity. The highly strained macrolactone could ultimately be closed under forcing Yamaguchi conditions. Comparison of the spectral data of the synthetic sample with those of authentic chagosensine methyl ester confirmed that the structure of this intriguing compound has been mis‐assigned by the isolation team.

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Language(s): eng - English
 Dates: 2018-08-032018-08-272018-10-08
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201808937
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Title: Angewandte Chemie International Edition
  Other : Angewandte Chemie, International Edition
  Other : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 57 (41) Sequence Number: - Start / End Page: 13575 - 13581 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851