236392-94-2Relevant articles and documents
Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB
Alam, Ashraful,Takaguchi, Yutaka,Ito, Hideyuki,Yoshida, Takashi,Tsuboi, Sadao
, p. 1909 - 1918 (2007/10/03)
The synthesis of mono-, di- and trisubstituted gallic acids and their ester with similar or different groups including different acetal and ketals is described. Regioselective bromination on two ortho-positions of methyl gallate, which is very crucial for many organic syntheses, was achieved in high yield and purity. The α- and β-DDB were synthesized in high overall yield and purity from the regioselective bromoderivatives.
Total Syntheses of the Metabolites of Schizandrin
Tanaka, Masahide,Ikeya, Yukinobu,Mitsuhashi, Hiroshi,Maruno, Masao,Wakamatsu, Takeshi
, p. 11703 - 11724 (2007/10/02)
The total syntheses of the metabolites of schizandrin were achieved.The tetracyclic lactone intermediates (13a-e) were prepared in optically pure form by the oxidative coupling reaction of the corresponding 3-benzyl-2-benzylidenebutyrolactones.Mukaiyama hydration of 13b afforded hydroxylactone (14), which was converted into SZ-M3 (4).The introduction of C6,7-diol moiety, which is common to the metabolites (4-11), was carried out by the successive double bond migration to 15a-e, lactone ring reduction ot the allylic diols (32a-e), and glycol formation.Then, reduction of the mesylates 33 completed the syntheses of the metabolites.