51138-07-9Relevant academic research and scientific papers
A short and efficient regioselective approach to the C-6 to C-19 segment of bifurcaranes and a formal total synthesis of β-microbiotene, microbiotol and cyclocuparanol
Srikrishna,Anitha Nagamani
, p. 3393 - 3394 (1999)
Employing an epoxide rearrangement based ring contraction reaction, a short and efficient regioselective approach to the C-6 to C-19 segment of the toluquinol substituted diterpenes bifurcaranes, and its extension to a formal total synthesis of the sesquiterpenes (±)-β-microbiotene, (±)-microbiotol and (±)-cyclocuparanol are described. The Royal Society of Chemistry 1999.
Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant
Cunningham, William B.,Tibbetts, Joshua D.,Hutchby, Marc,Maltby, Katarzyna A.,Davidson, Matthew G.,Hintermair, Ulrich,Plucinski, Pawel,Bull, Steven D.
supporting information, p. 513 - 524 (2020/02/13)
A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.
