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  An efficient route to the musk odorant (R,Z)-5-muscenone via base-metal-catalysis

Lehr, K., & Fürstner, A. (2012). An efficient route to the musk odorant (R,Z)-5-muscenone via base-metal-catalysis. Tetrahedron, 68(37), 7695-7700. doi:10.1016/j.tet.2012.05.085.

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 Creators:
Lehr, 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: Alkynes Iron catalysis Macrocycles Metathesis Molybdenum
 Abstract: Muscenone® is a valuable perfume ingredient consisting of a mixture of the E- and Z-isomers of 1 in racemic form as the major constituents. Among them, it is the (R,Z)-isomer, which exhibits the most favorable musk character and by far the lowest threshold; for these superior olfactory properties, pure (R,Z)-1 has recently been commercialized too. We present an efficient route to this precious compound based on an iron-catalyzed cross coupling reaction, a molybdenum-catalyzed alkyne metathesis for the formation of the macrocyclic ring, and a nickel-catalyzed semi-hydrogenation.

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Language(s): eng - English
 Dates: 2012-09-16
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.tet.2012.05.085
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: [Oxford : Pergamon
Pages: 6 Volume / Issue: 68 (37) Sequence Number: - Start / End Page: 7695 - 7700 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773
DOI: 10.1016/j.tet.2012.05.085