Dysideanone E等两类海绵杂萜的全合成研究

	Dysideanone E等两类海绵杂萜的全合成研究; Studies on the Total Synthesis of Two Kinds of Sponge-Derived Meroterpenoids Including Dysideanone E
	李阳明
导师	秦红波
摘要	This paper consists of three parts :(1) The application of Wieland–Miescher ketone in total synthesis; (2) Studies on synthesis of (±)-Dysifragilone A, B and (±)-Dysidavarone C; (3) Studies on the synthesis of (±)-Dysiherbol A and (±)-Dysideanone E. The first chapter is mainly about the application of Wieland–Miescher ketone in total synthesis. A 6/6- bicyclic skeleton, three functional groups and a chiral center, making it a very useful synthetic unit in total synthesis. Wieland–Miescher ketone is used as starting material in the synthesis of many terpenoids. In chapter 2, the total synthesis of (±) -Dysifragilone A, B and (±) -Dysidavarone C are reviewed. The synthetic route features an intramolecular reductive Heck reaction to construct the 6/5/6/6/-tetracycle of dysifragilones A and B and an intramolecular palladium-catalyzed α-arylation to forge the tetracyclo[7.7.1.02,7.010,15]heptadecane core structure of dysidavarone C from common intermediate. We used 5-bromovanillin as the starting material and synthesized the intermediate 2-bromo-3,4,6-trimethoxybenzyl bromide according to the literature. Subsequently, the benzyl bromide compound and Wieland–Miescher ketone derivatives undergo reductive alkylation to synthesize a common intermediate under the conditions of Birch reduction. The common intermediate first completed the synthesis of (±)-Dysifragilone A and B with the intramolecular reduction Heck reaction as the key reaction; then completed the synthesis of (±)-Dysidavarone C with the Pd-catalyzed carbonyl α-alkylation reaction as the key reaction. The synthesis route of (±)-Dysifragilone A was completed in 10 steps, with a total yield of 32%. The synthesis route of (±)-Dysifragilone B was completed in 10 steps, with a total yield of 44%. The synthesis of (±)-Dysidavarone C was completed in 9 steps with a total yield of 39%. In chapter 3, the total synthesis of (±) -Dysiherbol A and (±)-Dysideanone E are discussed. For the synthesis of (±) -Dysiherbol A, we designed the Heck reaction as the key reaction and conducted the exploration of total synthesis. As for the synthesis of (±) -Dysideanone E, free radical cyclization reaction is the key step, through 9 steps of reactions, the total yield is 6%.
	2021-11
文献类型	学位论文
条目标识符	http://ir.kib.ac.cn/handle/151853/74493
专题	昆明植物所硕博研究生毕业学位论文
推荐引用方式 GB/T 7714	李阳明. Dysideanone E等两类海绵杂萜的全合成研究, Studies on the Total Synthesis of Two Kinds of Sponge-Derived Meroterpenoids Including Dysideanone E[D],2021.

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