| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349186 | Tetrahedron: Asymmetry | 2010 | 5 Pages |
Enantioselective formal total syntheses of the marine trisnorsesquiterpenes clavukerin A and isoclavukerin A, starting from (R)-limonene employing an RCM reaction as the key step, are described.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
1-[(5S)-5-Isopropenyl-2-methylcyclopent-1-en-1-yl]pent-4-en-1-oneC14H20O[α]D24=+101.0 (c 4.6, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (5′S)
(7S)-6,10-Dimethylbicyclo[5.3.0]deca-1(10),5-dien-2-oneC12H16O[α]D25=-98.9 (c 2.5, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (7S)
(1R,7S,10S)-6,10-Dimethyl-11-oxatricyclo[5.4.0.01,10]undec-5-en-2-oneC12H16O2[α]D27=-82.1 (c 1.2, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (1R,7S,10S)
(1S,7S,10R)-6,10-Dimethyl-11-oxatricyclo[5.4.0.01,10]undec-5-en-2-oneC12H16O2[α]D24=-191.6 (c 2.5, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (1R,3S)
(1R,6S,7S,10S)-6,10-Dimethyl-11-oxatricyclo[5.4.0.01,10]-undecan-2-oneC12H18O2[α]D24=-34.3 (c 1.4, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (1R,6S,7S,10S)
(1S,6S,7S,10R)-6,10-Dimethyl-11-oxatricyclo[5.4.0.01,10]-undecan-2-oneC12H18O2[α]D26=-108.5 (c 5.7, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (1S,6S,7S,10R)
(1S,6R,7S,10R)-6,10-Dimethyl-11-oxatricyclo[5.4.0.01,10]-undecan-2-oneC12H18O2[α]D26=-80.6 (c 1.8, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (1S,6R,7S,10R)
