Total Synthesis Of (+)-Strictifolione And Model Study Of Garsubellin A

Contents of this paper can be divided into two parts,one is Total synthesis of(+)-Strictifolione and another is Model study of Garsubellin A.Chapter one is the total synthesis of(+)-Strictifolione.In this chapter,we first introduce the isolation,structure identification,physical activity,and the research progress on total synthesis of(+)-Strictifolione family compounds.On this basis,we have carried out the research of total synthesis of(+)-Strictifolione.Taking simple acrolein and 3-phenylpropyl aldehyde compounds as starting materials,we have successfully completed its convergent total synthesis in 4 steps and the overall yield is high up to 38%.The highlights of this synthesis list as follows: the olefin metathesis coupled two important segments(1,3-diol fragment and six-member lactone fragment);the PPTS catalytic cyclized reaction;and the indium intermediate Barbier reaction.Thus,we have reported a very convenient route to the synthesis of(+)-Strictifolione,which could be used in its family molecular.Our synthetic work avoided the repeated use of expensive Grubbs II catalyst,and developed the water as a reaction solvent,and opened up a highly efficient,simple path for the synthesis of natural products dihydro-Pyrones.Chapter two is model study of Garsubellin A.We first briefly introduced the separation,structural features,physical activity,as well as some related research of PPAPs family.Then we carried out a total synthesis of Garsubellin A.In order to improve the efficiency of synthesis,we first simplified and extracted skeletal structure which is common in this family.And we designed and synthesized a ring closure precursor.By screening different Lewis acid,the reaction temperature and solvent conditions,we successfully obtained the [3,3,1] bridged ring using the key Conia-ene reaction.Successful implementation of the method laid a solid foundation for the total synthesis Garsubellin A,while providing certain significance for the total synthesis of natural products PPAPs class.