100668-78-8Relevant academic research and scientific papers
Total Synthesis of (?)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone
Long, Yang,Ding, Yiming,Wu, Hai,Qu, Chunlei,Liang, Hong,Zhang, Min,Zhao, Xiaoli,Long, Xianwen,Wang, Shu,Puno, Pema-Tenzin,Deng, Jun
, p. 17552 - 17557 (2019)
The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy p-quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine-step total synthesis of (?)-perezoperezone from commercially available 3,5-dimethoxytoluene.
FORMAL TOTAL SYNTHESIS OF β-PIPITZOL
Sanchez, Ignacio H.,Larraza, Maria Isabel,Basurto, Fernando,Yanez, Ricardo,Avila, Salvador,et al.
, p. 2355 - 2359 (2007/10/02)
(+/-)-O-methylperezone (1b) was obtained by selective oxidative demethylation of (+/-)-leucoperezone trimethyl ether (4a).Compound (4a) was prepared by condensation of 2,3,5-trimethoxytoluene (5e) with 6-methyl-5-heptene-2-one, followed by reductive removal of the tertiary alcohol.The aromatic precursor 5e was prepared in four steps from 2,3-dimethoxytoluene (5a) and, alternatively, in three steps from 5-bromoveratraldehyde (6a).Racemic 1b and 4a were directly compared with the optically active molecules prepared from natural R(-)-perezone (1a).
