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The stereospecific synthesis of cis-β-bergamotene

✍ Scribed by Thomas W. Gibson; William F. Erman

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
237 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

Recently Bhattacharyya et al.

--(1) isolated a new sesquiterpene hydrocarbon from Indian valerian root oil, which was named S-bergamotene, and assigned structure 1. On the basis of a comparison of the chemical shift of the quaternary methyl group in g-bergamotene with the chemical shifts of the methyl groups in g-pinene, the stereochemistry as depicted by l_ was favored over the alteruative possibility 2. We wish to report an unambiguous synthesis ofA which serves to eliminate this structure for the natural material, and which suggests that natural g-bergamotene does indeed have the trans structure 2.

--Although the alcohol& may exist in two conformations, inspection of Ereiding models clearly suggests -the conformer showna. Measurement of the distance between the hydroxyl

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