| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346997 | Tetrahedron: Asymmetry | 2010 | 5 Pages |
The enantiospecific total synthesis of two epimers of the sesquiterpene isocalamusenone has been accomplished starting from the readily available monoterpene (R)-limonene, which of the natural product established the stereostructure and the absolute configuration.
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(3R,4S,6R,7S)-6,10-Dimethyl-3-(2-hydroxyprop-2-yl)bicyclo[5.3.0]dec-1(10)-en-4-olC15H26O2[α]D27=+62.8 (c 1.0, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (3R,4S,6R,7S)
(3S,6R,7S)-6,10-Dimethyl-3-(2-hydroxyprop-2-yl)bicyclo[5.3.0]dec-1(10)-en-4-oneC15H24O2[α]D26=-81.1 (c 1.6, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (3S,6R,7S)
(6R,7S)-3-Isopropylidine-6,10-dimethylbicyclo[5.3.0]dec-1(10)-en-4-oneC15H24O2[α]D28=-6.7 (c 0.7, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (6R,7S)
(6S,7S)-3-Isopropylidine-6,10-dimethylbicyclo[5.3.0]dec-1(10)-en-4-oneC15H22O[α]D24=+176.2 (c 0.5, CHCl3)Source of chirality: (R)-limoneneAbsolute configuration: (6S,7S)
