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  Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine

Gebauer, K., & Fürstner, A. (2014). Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine. Angewandte Chemie International Edition, 53(25), 6393-6396. doi:10.1002/anie.201402550.

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anie_201402550_sm_miscellaneous_information.pdf (Supplementary material), 3MB
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anie_201402550_sm_miscellaneous_information.pdf
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Supporting information
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Copyright Date:
2014
Copyright Info:
Wiley-VCH 69451 Weinheim, Germany
License:
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 Creators:
Gebauer, Konrad1, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: 1,4 additions; alkynes; metathesis; molybdenum; ruthenium
 Abstract: A sequence comprising a ring-closing alkyne metathesis of a propargyl alcohol derivative, followed by a ruthenium-catalyzed redox isomerization of the derived cycloalkyne and a transannular aza-Michael addition allowed the formation of the distinguishing piperidine-metacyclophane framework of the Lythraceum alkaloid lythanidine in a few high-yielding steps. This application attests to the excellent functional-group tolerance of a molybdenum alkylidyne complex endowed with triphenylsilanolate ligands, which enabled the macrocyclization even in the presence of protic functionalities, and thus illustrates the power of contemporary catalytic acetylene chemistry for target-oriented synthesis.

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Language(s): eng - English
 Dates: 2014-02-182014-05-122014-06-16
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201402550
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: 4 Volume / Issue: 53 (25) Sequence Number: - Start / End Page: 6393 - 6396 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851