1615-98-1Relevant academic research and scientific papers
Spiro-triterpenes from clay-catalysed rearrangement of hopenes: NMR structural elucidation and occurrence in a recent sediment
Hauke,Hauke, Verena,Trendel,Trendel, Jean M.,Albrecht,Albrecht, Pierre,Connan,Connan, Jacques
, p. 2227 - 2230 (1994)
Acidic K-10 montmorillonite clay-catalysed rearrangement of hop-22(29)-ene 5 and of hop-17(21)-ene 6 leads to the formation of small quantities of various fernenes and of new compounds, the 14-methyl-13,15-cyclo-B':A'-neo-26-nor-14,15-seco-18α-gammacer-7-ene 8 and its Δ8- and Δ9((11))-isomers 9 and 10, the structures of which have been established by MS and NMR spectroscopy. This novel hopane skeleton transposition also operates on bacterial sedimentary hopenes, as shown by GC-MS investigations of the alkene fraction from a recent lacustrine sediment.
Acid-Induced Rearrangement of Triterpenoid Hydrocarbons Belonging to the Hopane and Migrated Hopane Series
Ageta, Hiroyuki,Shiojima, Kenji,Arai, Yoko
, p. 2705 - 2716 (2007/10/02)
The acid-catalyzed rearrangement of triterpenoid monoenes belonging to the hopane and migrated hopane series with sulfuric acid and boron trifluoride etherate was investigated.By selecting the reaction conditions, a variety of the monoenes of these series, including three new compounds, 9βH-fern-7-ene (3c), 8βH-fern-9(11)-ene (4b), and adian-5(10)-ene (5b), were obtained.For comparison, oleanenes and migrated oleanenes were also subjected to the same reaction.Keywords--acid-induced rearrangement; triterpenoid hydrocarbon; hopane, migrated hopane; 9βH-fern-7-ene; 8βH-fern-9(11)-ene; adian-5(10)-ene; sulfuric acid; boron trifluoride
