Enantiospecific synthesis and confirmation of the relative and absolute stereostructure of 11-hydroxyguaiadienes

Enantiospecific total synthesis of two epimeric sesquiterpenes 11-hydroxyguaiadienes has been accomplished starting from the readily available monoterpene (R)-limonene, which confirmed the structure and absolute configuration of the natural products.

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1-[(6S,7S)-6,10-Dimethylbicyclo[5.3.0]deca-1(10),2-dien-3-yl]ethanone[α]D22=-103.7 (c 0.7, CHCl3).Source of chirality: (R)-limoneneAbsolute configuration: (6S,7S)C14H20O

2-[(6S,7S)-6,10-Dimethylbicyclo[5.3.0]deca-1(10),2-dien-3-yl]propan-2-ol[α]D26=-34.7 (c 1.0, CHCl3).Source of chirality: (R)-limoneneAbsolute configuration: (6S,7S)C15H24O

1-[(6R,7S)-6,10-Dimethylbicyclo[5.3.0]deca-1(10),2-dien-3-yl]ethanone[α]D24=-150.8 (c 1.1, CHCl3).Source of chirality: (R)-limoneneAbsolute configuration: (6R,7S)C14H20O

2-[(6R,7S)-6,10-Dimethylbicyclo[5.3.0]deca-1(10),2-dien-3-yl]propan-2-ol[α]D26=-55.1 (c 1.1, c 0.5, CHCl3).Source of chirality: (R)-limoneneAbsolute configuration: (6R,7S)C15H24O