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  Formal Total Synthesis of Kendomycin by Way of Alkyne Metathesis/Gold Catalysis

Hoffmeister, L., Persich, P., & Fürstner, A. (2014). Formal Total Synthesis of Kendomycin by Way of Alkyne Metathesis/Gold Catalysis. Chemistry - A European Journal, 20(15), 4396-4402. doi:10.1002/chem.201304580.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0019-DA84-D Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0019-FD00-C
Genre: Journal Article

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chem_201304580_sm_miscellaneous_information.pdf (Supplementary material), 5MB
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chem_201304580_sm_miscellaneous_information.pdf
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Supporting information
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application/pdf / [MD5]
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Copyright Date:
2014
Copyright Info:
Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
License:
-

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 Creators:
Hoffmeister, Laura1, Author              
Persich, Peter1, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: alkynes; gold; metathesis; molybdenum; natural products
 Abstract: In an attempt to study the ability of the latest generation of alkyne metathesis catalysts to process sterically hindered substrates, two different routes to the bacterial metabolite kendomycin (1) were explored. Whereas the cyclization of the overcrowded arylalkyne 39 and related substrates turned out to be impractical or even impossible, ring closure of the slightly relaxed diyne 45 was achieved in excellent yield under notably mild conditions with the aid of the molybdenum alkylidyne 2 endowed with triphenylsilanolate ligands. The resulting cycloalkyne 46 was engaged into a gold-catalyzed hydroalkoxylation, which led to benzofuran 47 that had already previously served as a late-stage intermediate en route to 1.

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Language(s): eng - English
 Dates: 2014-03-032014-04-07
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201304580
 Degree: -

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Title: Chemistry - A European Journal
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: 7 Volume / Issue: 20 (15) Sequence Number: - Start / End Page: 4396 - 4402 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058