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Journal Article

Ring closing alkyne metathesis: stereoselective synthesis of civetone

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Seidel,  Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-3C01-6
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.