| Baculiferin L is a kind of alkaloids that extracted from Sponge lotrochota Baculifera in the South China Sea,which has novel structure and shows significantly physiological activity target on HIV-1 and tumor.But its content is very low in the sponge,can not be isolated to extract large quantities,limiting their pharmacological activity confirmed and further pharmacological research,so the synthesis of Baculiferin L has vital practical significance.In this paper,progress in AIDS,cancer and synthesis of alkaloids Lamellarin type was first reviewed.We choose the AgOAc synthesis route that is more mature studied to amplify technology research,completed Intermediate 5 and 9 process optimization,improved the intermediate yield and selectivity.But in the critical oxidation reaction of cyclization pyrrole ring(intermediate 6),the repeated study shows that the amplification process yields only reach 5.5%,less than 56 percent that of the reference reported,so we gave up this route.Then we switched to study and explore the synthesis of intermediate 6 with Barton-Zard condensation.3,4-dimethoxybenzaldehyde was used to synthesis of compound 16 through Henry condensation the,yield 82%,Compound 16 was reacted with Br2 to synthesis of compound 17,yield 79.4%,Compound 17 and 3,4-dimethoxybenzene boronic acid was used to synthesised compound 18 through coupling reaction,yield 65%.But in the synthesis 19 reaction we found the highest yields only reach 10%.Finally,unable to break through in Barton-Zard condensation we turn to Leusen condensation.After several years of research we found that pyrrole ring together is the key to the entire synthesis process.So we first synthesised the pyrrole ring.In this route we finished the synthesis of the pyrrole ring intermediate 21 and 25,yields 71.2%and 69.5%respectively,completed the synthesis of 22,yield 97%;Because of the time I could not continuing the route,but if Leusen condensation can break through,the route would be promising. |
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