[Total synthesis of schizandrin, the main active ingredient isolated from the Chinese herbal medicine fructus schizandrae].
In this paper, schizandrin(9), the main active ingredient isolated from Schisandra chinensis, was synthesized from gallic acid by a new route. This route consists of only nine steps, including reductive-coupling reaction of compound(5) and dehydryoxylatic reaction of compound(6) to give compounds(7Z, 7E). By hydroboration, compound (8) was obtained from compound(7Z). With the presence of thallium trifluoroacetate (TTFA) and 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) compound (9) is obtained from compound (8) by intramolecular nonphenolic oxidative coupling. These compounds were identified by elemental analysis, MS, UV, IR and NMR spectra.
Chang
J
J
Henan Institute of Chemistry, Zhengzhou 450003.
Xie
J
J
D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D032141:Schisandra / Q000737:chemistry*
D034242:Cyclooctanes; D017705:Lignans; D011083:Polycyclic Compounds; C011105:schizandrin