title: Efficient Synthesis of the Cyclopentanone Fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione.
abstract: This paper describes the selective syntheses of twocis-isomer enriched cyclopentanone fragrances: (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone (4 steps, 62% overall yield, 67%cis) and Magnolione®(5 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-enriched3and4.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Guojun
authors.initials: G
authors.lastname: Pan
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA ; University of Colorado Cancer Center, Aurora, CO 80045, USA.
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
keywords: cis-selective synthesis; cyclopentanone fragrances; jasmonoids; kinetic resolution; magnolione
references.citation: J Org Chem. 2005 Jun 10;70(12):4876-8
references.pmid: 15932335
references.citation: J Am Chem Soc. 2007 Feb 14;129(6):1498-9
references.pmid: 17283985
references.citation: Leukemia. 2002 Apr;16(4):608-16
references.pmid: 11960340
references.citation: J Am Chem Soc. 2002 Mar 20;124(11):2458-60
references.pmid: 11890793
references.citation: J Org Chem. 2012 May 18;77(10):4801-11
references.pmid: 22519642
references.citation: J Am Chem Soc. 2002 Aug 28;124(34):9992-3
references.pmid: 12188655
references.citation: Org Lett. 2008 Aug 7;10(15):3271-3
references.pmid: 18582066
references.citation: J Org Chem. 2001 Jul 13;66(14):4814-8
references.pmid: 11442410
references.citation: Angew Chem Int Ed Engl. 2000 Sep 1;39(17):2980-3010
references.pmid: 11028024
references.citation: Trends Genet. 2003 Jul;19(7):409-13
references.pmid: 12850447
references.citation: J Am Chem Soc. 2003 May 28;125(21):6388-90
references.pmid: 12785777