60234-80-2Relevant academic research and scientific papers
Synthetic Studies on Aromatic Sesquiterpenoids: Synthesis of Curcumene Ether by Olefin Cyclisation
Kametani, Tetsuji,Kawamura, Kuniaki,Tsubuki, Masayoshi,Honda, Toshio
, p. 1305 - 1310 (2007/10/02)
The acid-catalysed cyclisation of the olefinic β-hydroxy sulphides (15a) and (15b) gave 3-phenylthiocurcumene ether as a diastereoisomeric mixture together with 5,5-dimethyl-4-phenylthio-1-p-tolylcyclohex-1-ene (16) and 2-methyl-3-(1-methyl-1-phenylthioethyl)-2-p-tolylcyclobutan-1-ol (19).The diastereoisomers (17) and (18) were converted into curcumene ether (24).Treatment of the silyl enol ether (7) with benzenesulphenyl chloride yielded 5-phenylthiomethyl-2-tetrahydrofuran (8) and 5-chloro-1,6-bis(phenylthio)-1-p-tolylhexan-2-one (9). 1-p-Tolylhexane-2,5-dione (10) was also synthesised from (5) employing a palladium-catalysed oxidation, and this result constitutes a formal total synthesis of cuparene (11).
