Naturally occurring secondary metabolites cuparenes (1a-b) and herbertenes (1c) are sesquiterpenes with a cyclopetanoid backbone and (-)-ar-teunifolene (3a) contains a cyclohexane backbone. They possess vicinal all-carbon quaternary centers, including at least one stereogenic quaternary centre situated at the pseudobenzylic position. (R)-(+)-cuparene (1a) was isolated in 1958 by Erdtman et. al1 from the essential oil of leaves from Thujaorientallis. (R)-enantiomer of (+)-cuparenone (1b) was isolated from the liverworts Mania fragrans by Benesova et. al2. In 2004, (-)-ar-teunifolene (3a) was isolated by König and co-workers3 from the essential oil of the east African sandalwood Osyris tenuifolia. These compounds are used to treat fungal infections, cancer, coughs, hemorrhages, excessive menstruation, bronchitics, asthma, and arthritic pains.

Catalytic Asymmetric Total Syntheses of (+)-a-Cuparenone, (+)-Cuparene, (+)-Herbertene and (-)-ar-Tenuifolene

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27th CRSI National Symposium in Chemistry

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