Tobacco Chemistry. 55. Three New Cembranoids from Greek Tobacco. The Stereochemistry of (1S,2E,4S,6R,7E,11E)-2,7,11-Cembratriene-4,6-diol.
- 1 January 1982
- journal article
- research article
- Published by Danish Chemical Society in Acta Chemica Scandinavica
- Vol. 36b (3) , 147-153
- https://doi.org/10.3891/acta.chem.scand.36b-0147
Abstract
Three new diterpenoids were isolated from tobacco. The 1st was identified as (1S,2E,4S,6R,7E,11S)-2,7,12(20)-cembratriene-4,6,11-triol (3) by X-ray analysis and chemical correlation, the 2nd was formulated as (1S,2E,4S,6R,7E,10E,12S)-2,7,10-cembratriene-4,6,12-triol (4) by spectral and chemical methods, while the 3rd, (1S,2E,4S,6R,7E,11S,12S)-11,12-epoxy-2,7-cembradiene-4,6-diol, previously described as a synthetic product, is now reported as a tobacco constituent. The configuration at C-6 in (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (2) was resolved by chemical correlation with triol 3. The biogenesis of the 2 new triols (3, 4) is discussed in the light of results obtained by singlet O2 reactions.This publication has 2 references indexed in Scilit:
- Tobacco Chemistry. 54. (1S,2E,4S,6E,8S,11R,12S)-8,11-Epoxy-2,6-cembradiene-4,12-diol, a New Constituent of Greek Tobacco.Acta Chemica Scandinavica, 1982
- Tobacco Chemistry. 51. New Cembranic Diterpenoids from Greek Tobacco.Acta Chemica Scandinavica, 1980