Study On The Synthesis Of Aldingenin

R-Carvone is found naturally in many essential oils. R-Carvone is often used as starting material in organic synthesis because of cheap, readily available, and having a chiral center. Aldingenin A is one of the four sesquiterpenoids (Aldingenin A, B, C, D), which were isolated from newly discovered red algae in Brazilian Atlantic by Lagoc in2003. There is no published research towards the total synthesis of this compound and its absolute configuration has not been determined yet. Inferring from the spectral data of this molecule, it is a bromo-substitutional sesquiterpenoid which bear four rings and7chiral centers, four of which are contiguous chiral carbon. The unique structure espeacially four oxygen heterocyclic rings might make it special in biological activity. Its bromine atom makes it easier to connect with other functional groups, such as glycosides, amino acids and other functional groups. These groups can improve the water solubility, which also might bring it some high physiological activity. No matter for organic synthetic research or medicinal chemistry research, this study has important academic significance.This thesis is going to explore the approach for a new synthesis of Aldingenin A and confirm its absolute configuration by using R-Carvone as the starting material. We hope to provide the foundation for the synthesis of Aldingenin B, C, D. We explored three synthetic routes towards the synthesis of skeletal structure of Aldingenin A, and some progress have been made in each route.The first chapter summarizes the applications of R-carvone in organic synthesis. The second chapter introduces our studies on the synthesis of Aldingenin A from R-carvone. Experimental part and physical data for compounds described in chapter2are recorded in chapter3.Our strategy and progress for the synthesis of Aldingenin is shown in Scheme1.