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  Ring closing alkyne metathesis: stereoselective synthesis of civetone

Fürstner, A., & Seidel, G. (2000). Ring closing alkyne metathesis: stereoselective synthesis of civetone. Journal of Organometallic Chemistry, 606(1), 75-78. doi:10.1016/S0022-328X(00)00096-6.

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 Creators:
Fürstner, Alois1, Author              
Seidel, Günter1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: Alkylidynes; Alkynes; Macrocycles; Metathesis; Molybdenum; Tungsten
 Abstract: A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)3WΞCCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)6 and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate.

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Language(s): eng - English
 Dates: 1999-12-172000-07-14
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/S0022-328X(00)00096-6
 Degree: -

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Title: Journal of Organometallic Chemistry
  Other : J. Organomet. Chem.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Amsterdam : Elsevier
Pages: 4 Volume / Issue: 606 (1) Sequence Number: - Start / End Page: 75 - 78 Identifier: ISSN: 0022-328X
CoNE: https://pure.mpg.de/cone/journals/resource/954925622228