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  Increasing the Structural Span of Alkyne Metathesis

Persich, P., Llaveria, J., Lhermet, R., de Haro, T., Stade, R., Kondoh, A., et al. (2013). Increasing the Structural Span of Alkyne Metathesis. Chemistry – A European Journal, 19(39), 13047-13058. doi:10.1002/chem.201302320.

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[310]SI.pdf (Supplementary material), 12MB
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2013
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Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
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 Creators:
Persich, Peter1, Author           
Llaveria, Josep1, Author           
Lhermet, Rudy1, Author           
de Haro, Theresa1, Author           
Stade, Robert1, Author           
Kondoh, Azusa1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: alkyne metathesis; gold; molybdenum; natural products; total synthesis; transannular reactions
 Abstract: A new generation of alkyne metathesis catalysts, which are distinguished by high activity and an exquisite functional group tolerance, allows the scope of this transformation to be extended beyond its traditional range. They accept substrates that were previously found problematic or unreactive, such as propargyl alcohol derivatives, electron-deficient and electron-rich acetylenes of various types, and even terminal alkynes. Moreover, post-metathetic transformations other than semi-reduction increase the structural portfolio, as witnessed by the synthesis of a annulated phenol derivative via ring-closing alkyne metathesis (RCAM) followed by a transannular gold-catalyzed Conia-ene reaction. Further examples encompass a post-metathetic transannular ketone–alkyne cyclization with formation of a trisubstituted furan, a ruthenium-catalyzed redox isomerization, and a Meyer–Schuster rearrangement/oxa-Michael cascade. These reaction modes fueled model studies toward salicylate macrolides, furanocembranolides, and the cytotoxic macrolides acutiphycin and enigmazole A; moreover, they served as the key design elements of concise total syntheses of dehydrocurvularin (27) and the antibiotic agent A26771B (36).

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Language(s): eng - English
 Dates: 2013-06-182013-09-032013-09-23
 Publication Status: Published in print
 Pages: 12
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201302320
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: 12 Volume / Issue: 19 (39) Sequence Number: - Start / End Page: 13047 - 13058 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058