Studies On The Total Synthesis Of (±)-Yaequinolone A2 And Its Analogues

This thesis main focused on the total syntheses of(±)-Yaequinolone A2 as well as its analogues—Yaequinolone J1 and J2.Meanwhile,the coupling between sildenafil and bromomethyl acetate is also studied.It is consisted of the following four parts:Chapter1.The progress on the study of Vinylogous Aldol Reaction(review)The review introduced some general example of Vinylogous Aldol reactions and application in syntheses,meanwhile,its mechanism,reaction condition and new reagents also were discussed.Chapter2.Total syntheses of(±)-Yaequinolone A2The definition,classification of Yaequinolones A2 was introduced briefly.A concise total synthesis of(±)-yaequinolone A2 has been accomplished through 6 steps from anthranilic acid.Tandem and asymmetric synthesis of yaequinolone A2 was also studied.Chapter3.The primary studies on the total synthesis of(±)-Yaequinolone J1 and J2The key intermediates,(2-amino-6-hydroxyphenyl)(4-methoxyphenyl)methanone and(2-methoxyacetamide-6-hydroxyphenyl)(4-methoxyphenyl)methanone,have been accomplished through 7 steps and 8 steps from 3-aminophenol respectively.The reactions of the two intermediates with citral are currently being carried out.Chapter4.The studies on the coupling of sildenafil and bromomethyl acetateThe coupling of sildenafil and bromomethyl acetate gave substituted product at N 6 position under strong basic conditions and the structure of the product was determined by X-Ray data.