Synthesis of 2,15-hexadecanedione as a precursor of Muscone

Yinjuan Bai; Jun Lu; Zhen Shi; Bingqin Yang

doi:10.1055/s-2001-12339

Synlett 2001; 2001(4): 0544-0546
DOI: 10.1055/s-2001-12339

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Synthesis of 2,15-hexadecanedione as a precursor of Muscone

Yinjuan Bai^* , Jun Lu, Zhen Shi, Bingqin Yang

^*Department of Chemistry, Northwest University, Xi'an 710069, P. R. China; E-mail: lujunyue@hotmail.com

Abstract

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Muscone is a precious fragrant compound, which is scarce in nature, many synthetic attempts for this unique natural product have been carried out. A new synthetic method for 2,15-hexadecanedione, a precursor of muscone, from imidazalium salt and di-Grignard reagent is reported. Imidazalium salt was used as tetrahydrofolate coenzyme model at formic acid oxidation level and di-Grignard reagent as nucleophile to which one-carbon unit was transferred, the biomimetic synthesis of 2,15-hexadecanedione was successfully accomplished by using the addition-hydrolysis reaction of imidazolium salt with di-Grignard reagent. A novel method for preparing muscone is provided.

biomimetic synthesis - muscone - 2,15-hexadecanedione - tetrahydrofolate coenzyme model - di-Grignard reagent

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