111194-05-9Relevant articles and documents
Asymmetric total synthesis of (+)-ovafolinins A and B
Fang, Xianhe,Shen, Lei,Hu, Xiangdong
, p. 7539 - 7541 (2018)
(+)-Ovafolinins A and B are two homologous lignans containing unique polycyclic skeletons. Benefiting from a highly diastereoselective alkylation of (S)-Taniguchi lactone, a double Friedel-Crafts reaction, a global debenzylation and a Cu(OAc)2-
Synthesis of lyoniresinol with combined utilization of synthetic chemistry and biotechnological methods
Takemoto, Masumi,Fukuyo, Ayako,Aoshima, Yoichi,Tanaka, Kiyoshi
, p. 226 - 229 (2007/10/03)
We have synthesized lyoniresinol with the combined utilization of synthetic chemistry and biotechnological methods, specifically using plant cell cultures as an "enzyme source."
Asymmetric synthesis of lignans using oxazolidinones as chiral auxiliaries
Charlton, James L.,Chee, Gaik-Lean
, p. 1076 - 1083 (2007/10/03)
A simple procedure for the asymmetric synthesis of lignans via chiral β-benzyl-γ-butyrolactones has been developed. The key benzylbutyrolactone intermediates were efficiently synthesized using a six-step procedure, starting from 3,4-(methylenedioxy)cinnamic acid. The key step in this sequence was a highly diastereoselective alkylation of an N-acyloxazolidinone enolate. The resulting β-benzyl-γ-butyrolactones were subsequently transformed into the benzylidene lignans gossypifan and savinin (hibalactone) via aldol condensation-dehydration reactions, and into the dibenzylbutyrolactone lignan 4′-demethylyalein, through alkylation. Oxidation of 4′-demethylyatein with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) afforded cis- and trans-benzylidenebenzylbutyrolactones, whereas oxidation with DDQ/TFA gave 4′-demethyl-deoxyisopodophyllotoxin.