Correction of the structure of a new sesquiterpene from Cistus creticus ssp. creticus.
In an attempt to identify the structure of a sesquiterpene from Cistus creticus ssp. creticus proposed in the literature as 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4alpha,5,8,8alpha-octahydronaphthalene, the synthesis of its cis isomer 2 was carried out in 11 steps and 9.5% yield. Comparison of the spectra of 2 and those reported earlier for the synthetic trans isomer 1 with the spectral profile of the isolated natural product indicated that the latter was not compatible with either 1 or 2. The correct structure was assigned, by detailed spectroscopic analysis of the natural product, as 6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (3).
Hatzellis
Konstantinos
K
Department of Chemistry, University of Crete, Heraklion 71409, Crete, Greece.
Pagona
Georgia
G
Spyros
Apostolos
A
Demetzos
Costas
C
Katerinopoulos
Haralambos E
HE
D002384:Catalysis; D029758:Cistus / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C496937:6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene; D007202:Indicators and Reagents; D009281:Naphthalenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C437376:drimane