Efficient synthesis of the cyclopentanone fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione |
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Authors: | Guojun Pan Robert M. Williams |
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Affiliation: | 1. Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA;2. University of Colorado Cancer Center, Aurora, CO 80045, USA |
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Abstract: | This paper describes the selective syntheses of two cis-isomer-enriched cyclopentanone fragrances: (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone (four steps, 62% overall yield, 67% cis) and Magnolione® (five steps, 60% overall yield, 55% cis). In addition, the asymmetric synthesis of (3aR,7aS)-5-methyl-2,3,3a,4,7,7a-hexahydro-1H-inden-1-one as well as (3a′R,7a′S)-5′-methyl-2′,3′,3a′,4′,7′,7a′-hexahydrospiro[[1,3]dioxolane-2,1′-indene] has been realized by an efficient kinetic resolution, which enables the selective synthesis of the 2S,3R-isomer-enriched 3 and 4. |
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Keywords: | Cyclopentanone fragrances Jasmonoids Magnolione® Cis-selective synthesis Kinetic resolution |
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