This research paper is aimed at studying the total synthesis of pharmacologically active lignan(–)-hinokinin.The synthesis features a three-step cascade reaction involving highly stereoselective Michael addition,anio...This research paper is aimed at studying the total synthesis of pharmacologically active lignan(–)-hinokinin.The synthesis features a three-step cascade reaction involving highly stereoselective Michael addition,anion-oxidative hydroxylation,and oxygen anion cyclization to construct the pivotal butyrolactonimidate intermediate.展开更多
The fruits of Piper cubeba have been used in Ayurvedic system of medicine for pain,tastelessness, painful urination and mouth diseases. Among its various chemical constituents,（-）-hinokinin, a trypanosomicidal diben...The fruits of Piper cubeba have been used in Ayurvedic system of medicine for pain,tastelessness, painful urination and mouth diseases. Among its various chemical constituents,（-）-hinokinin, a trypanosomicidal dibenzylbutyrolactone lignan, is found in significant quantities.For quality evaluation of P. cubeba fruit and its commercial formulations, there is an urgent need to develop an analytical method based on（-）-hinokinin. For this purpose, an HPLC method was developed using photo diode array detector and Waters HR C18 column with gradient elution consisting of water and acetonitrile. The developed method was validated as per ICH-Q2 B guidelines and found to be accurate, precise and linear over a wide range of concentrations（5–300 mg/m L）.（-）-Hinokinin contents were found to be in the range of 0.005–0.109%（m/m） in various P. cubeba samples. The developed method was extended to LC–MS for further identification and characterization of（-）-hinokinin in samples. The developed method is simple,rapid and specific, and can be used as a tool for quality control of P. cubeba fruits and its commercial formulations.展开更多
A convenient and rapid approach for the syntheses of (-)-kaerophyllin (1),(-)-hinokinin (2) and (±)-isohinokinin (3) was described. The key steps were involved in condensation of aromatic aldehyde and alkylation ...A convenient and rapid approach for the syntheses of (-)-kaerophyllin (1),(-)-hinokinin (2) and (±)-isohinokinin (3) was described. The key steps were involved in condensation of aromatic aldehyde and alkylation of the resulting ester to give the complete skeleton of dibenzylbutyrolactone-lignan. Hydrolysis,followed by resolution with quinine,reduction and when appropriate,oxidation gave the title compound. The asymmetric total synthesis of the kaerophyllin (1) was reported for the first time.展开更多
基金We acknowledge grant supports from Chongqing University,and the Fundamental Research Funds for the Central Universities(Project No.0236015202004).
文摘This research paper is aimed at studying the total synthesis of pharmacologically active lignan(–)-hinokinin.The synthesis features a three-step cascade reaction involving highly stereoselective Michael addition,anion-oxidative hydroxylation,and oxygen anion cyclization to construct the pivotal butyrolactonimidate intermediate.
文摘The fruits of Piper cubeba have been used in Ayurvedic system of medicine for pain,tastelessness, painful urination and mouth diseases. Among its various chemical constituents,（-）-hinokinin, a trypanosomicidal dibenzylbutyrolactone lignan, is found in significant quantities.For quality evaluation of P. cubeba fruit and its commercial formulations, there is an urgent need to develop an analytical method based on（-）-hinokinin. For this purpose, an HPLC method was developed using photo diode array detector and Waters HR C18 column with gradient elution consisting of water and acetonitrile. The developed method was validated as per ICH-Q2 B guidelines and found to be accurate, precise and linear over a wide range of concentrations（5–300 mg/m L）.（-）-Hinokinin contents were found to be in the range of 0.005–0.109%（m/m） in various P. cubeba samples. The developed method was extended to LC–MS for further identification and characterization of（-）-hinokinin in samples. The developed method is simple,rapid and specific, and can be used as a tool for quality control of P. cubeba fruits and its commercial formulations.
文摘A convenient and rapid approach for the syntheses of (-)-kaerophyllin (1),(-)-hinokinin (2) and (±)-isohinokinin (3) was described. The key steps were involved in condensation of aromatic aldehyde and alkylation of the resulting ester to give the complete skeleton of dibenzylbutyrolactone-lignan. Hydrolysis,followed by resolution with quinine,reduction and when appropriate,oxidation gave the title compound. The asymmetric total synthesis of the kaerophyllin (1) was reported for the first time.
