Chiral Pentlactone In The Synthesis Studay Of Mintlactone And Isomintlactone

The rational utilization of resource compounds is one main task of our research group.Based on the reaseach results of rational utilization of the abundant steroidal sapogenins,a new degradated method for steroidal sapogenin was developed by us,and 4(R)-methyl-tetrahydropyran-2-one was easily obtained from the degradation.Our group is focused in how to utilize 4(R)-methyl-tetrahydropyran-2-one in organic synthesis.Mintlactone and Isomintlactone is one of the effective components in the mint oil.Because of their low content,it is valuable to synthesize them by organic chemistry.My dissertation is focused on synthesis research of mintlactone and isomintlactone,which was transformed from the 4(R)-methyl-tetrahydropyran-2-one:1.Introduced the source,the synthesis and the economic value of the mintlactone and isomintlactone.And summarized the synthesis of mintlactone and isomintlactone by consulting the literatures,which was classified by the different material. 2.Synthesized some important intermediates of mintlactone and isomintlactone as the methods in the literatures.For examples: 4(R)-methyl-tetrahydropyran-2-one,MOMOM,MOMCl etc.3.Accomplished the synthesis of the bicyclic skeleton of the mintlactone and isomintlactone.First,utilized the 4(R)-methyl-tetrahydropyran-2-one as our material,and then reduced by LAH.After protecting by the MOMCl,the nucleophilic substituent reaction was taken by the negative ion of the 1,3-dithone and then deprotected the MOM group.Through oxidation and Witting reaction, we completed the synthesis of the whole carbon skeleton.In the next place,we attempted to get the cycle skeleton by inter molecular Michael addition and SmI₂ reaction.Finally,accomplished the synthesis of the cycle skeleton of the mintlactone and isomintlactone by the SmI₂ reaction.