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A Chemical Study of Virginia Tobacco Flavour (Nicotiana tabacum L.) II. Isolation and synthesis of cis-2-isopropenyl-8-methyl-1,2,3,4-tetrahydro-1-naphthalenol and 3-isopropenyl-5-methyl-1,2-dihydronaphthalene

✍ Scribed by Edouard Demole; Paul Enggist

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
438 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Gas liquid chromatography allowed isolation of the novel cis‐2‐isopropenyl‐8‐methyl‐1,2,3,4‐tetrahydro‐1‐naphthalenol (A) and its dehydration product, 3‐isopropenyl‐5‐methyl‐1,2‐dihydronaphthalene (B), from two small subfractions of Virginia tobacco condensate. Both these norsesquiterpenes were identified on spectral grounds and synthesized from 1‐methylnaphthalene in a way (9 steps) that also afforded the «non‐natural», trans‐alcohol A′. The possible biogenesis of A and B in tobacco is briefly outlined.

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