Study On Total Synthesis Of Rauvomine Monoterpene Alkaloids

Anti-inflammatory monoterpene indole alkaloid Rauvomine B?2?features an unusual6/5/6/6/3/5 hexcyclic skeleton.Its structure is yet to be finally confirmed by X-ray crystallography.In addition,the family compound also has certain Anti-inflammatory activity,which has attracted the interest of synthetic chemists.The total synthetic work of 2 is expected to establish the construction method of this novel skeleton structure,to confirm its chemical structure,and in addition,to contribute to the discovery of new bioactive materials led by natural products.Applying synthetic chemistry as a means,using tryptophan methyl ester hydrochloride?6?as the starting material,the current study completed the key pentacyclic structure 31 and 55 over 10 steps in an overall yield of 2.8%.The key steps were to build the 3^rd,4^thh and 5^th ring via asymmetric Pictet-Spengler?Dieckmann condensation and Mukaiyama aldol reaction,respectively.So far,we are exploring the use of important skeleton fragments 31 on the hand for Wittig,methylation and other reactions to complete the final synthesis.