140848-14-2Relevant academic research and scientific papers
Cyclization and Rearrangements of Farnesol and Nerolidol Stereoisomers in Superacids
Polovinka, Marina P.,Korchagina, Dina V.,Gatilov Yurii V.,Bagrianskaya Irina Yu.,Barkhash, Vladimir A.,et al.
, p. 1509 - 1517 (1994)
Acid-catalyzed cyclization of 2,3-trans- and 2,3-cis-farnesol proceeds regioselectively and stereospecifically, yielding drimenol and epi-drimenol, respectively.The trans and cis isomers of nerolidol undergo carbo- and heterocyclization reactions.The trans isomer gives tricyclic caged hydrocarbons with new skeletal types, while the rearrangements of the cis isomer produce derivatives of 2-oxabicyclodecane.The ICAR computer program was used to derive reasonable mechanisms for the acid-catalyzed transformations of nerolidol, and the probability of the mechanisms was evaluated by the molecular mechanics method.
CYCLIZATION OF ACYCLIC ISOPRENOIDS V REARRANGEMENT OF STEREOISOMERIC FARNESOLS AND NEROLIDOLS IN SUPERACIDS
Polovinka, M. P.,Unzur, N. D.,Perutskii, V. B.,Korchagina, D. V.,Gatilov, Yu. V.,et al.
, p. 1871 - 1885 (2007/10/02)
The cyclization of 2,3-trans- and -cis-farnesols in superacids is structurally selective and stereospecific, giving drimenol and epidrimenol respectively.Depending on the reaction conditions, trans- and cis-nerolidols undergo carbo- or hetero-cyclization, to give in the first case tricyclic bridged hydrocarbons with a novel skeleton, and in the second case a 2-oxabicyclodecane.
