88034-06-4Relevant academic research and scientific papers
Superacidic low-temperature cyclization of terpenols and their acetates
Vlad, P. F.,Ungur, N. D.,Nguen Van Hung,Perutsky, V. B.
, p. 2391 - 2403 (2007/10/03)
The superacidic low-temperature cyclization of terpenols and their acetates be fluorosulfonic acid represents a highly efficient chemo- and structurally selective and stereospecific process.Homoallylic alcohols (α-isomers of cycloterpenols) are the products of cyclization of terpenols; the configuration of the hydroxymethyl group in the products is predetermined by the configuration of the allylic double bond in aliphatic or partially cyclized precursors.The cyclization of terpenyl acetates yields monoacetates of fully cyclized diastereomeric primary-tertiary γ-diols.Their stereochemistry also depends on the configuration of the allylic double bond in the starting substrates. - Key words: terpenols; terpenyl acetates; cyclization, fluorosulfonic acid, drimanes, isoagathanes, scarlanes.
CYCLIZATION AND REARRANGEMENT OF DITERPENOIDS. SYNTHESIS OF Δ12 - AND Δ13(14)-ISO-20-DEOXYLUTEONES
Vlad, P. F.,Ungur, N. D.
, p. 752 - 759 (2007/10/02)
Δ12- and Δ13(14)-Iso-20-deoxyluteones have been synthesized from 13E- and 13Z- bicyclogeranylgeranylacetones.The latter were reduced to the corresponding alcohols, which were acetylated, and the acetates obtained were cyclized with fluorosulfonic acid in nitropropane.The reaction product was saponified to a mixture of tricyclic alcohols which were oxidized with the chromium trioxide-pyridine complex to a mixture of Δ12- and Δ13(14)-iso-20-deoxyluteones and this was separated chromatographically.
