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. 2014 Jan 14;70(2):276-279.
doi: 10.1016/j.tet.2013.11.066.

Efficient Synthesis of the Cyclopentanone Fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione

Guojun Pan  1 , Robert M Williams  2
Affiliations

Efficient Synthesis of the Cyclopentanone Fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione

Guojun Pan et al. Tetrahedron. .

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 (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-enriched 3 and 4.

Keywords: cis-selective synthesis; cyclopentanone fragrances; jasmonoids; kinetic resolution; magnolione.

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Figures

Figure 1
Figure 1
Structures of some jasmonoid fragrances.
Scheme 1
Scheme 1
Synthesis of keto-aldehyde 8.
Scheme 2
Scheme 2
Syntheses of 3 and 4.
Scheme 3
Scheme 3
Sharpless asymmetric dihydroxylation of (±)-7 (1.94 g scale).
Scheme 4
Scheme 4
Synthesis of (+)-10 from (+)-7.
See this image and copyright information in PMC

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