天然产物β-funebrene的全合成

天然产物及其衍生物是生物活性分子的重要来源，天然产物的发现、合成和活性研究对人类的生活和健康具有重大意义，例如人类在天然产物中发现抗疟疾活性分子奎宁和青蒿素、抗肿瘤活性分子紫杉醇等，以及在活性天然产物基础上发展的氯喹、蒿甲醚、艾瑞布林等都极大的推动了相关疾病的治疗研究，给人们的生命健康提供了重要保障。同时天然产物全合成作为有机化学的重要分支之一，也促进了有机化学等相关学科的发展。

高张力结构普遍存在于天然产物中，使得天然产物显示独特的生物活性，反式5/5并环结构就是高张力结构的代表之一。虽然反式5/5并环的天然产物在自然界中数量有限，但该类天然产物独特的活性以及较高的合成挑战性吸引了科学家的关注。但因其较高的合成难度，对反式5/5并环的合成研究报道较少，这些因素限制了对含有该类结构天然产物的活性研究。

本论文的研究目标是含有高张力反式5/5并环的天然产物β-funebrene就是其中的代表。在研究过程中，本文首先对目前已报道的反式5/5并环的合成策略做了简单总结。在此基础上，以课题组发展的分子内[3+2]环化反应为核心策略，一步构建反式5/5并环。随后采用aldol反应成功构建六元环，再经过两步官能团转化实现了天然产物β-funebrene的全合成，为接下来进一步的活性研究提供了物质基础。

Natural products and their derivatives are an important source of biologically active molecules. The discovery, synthesis and activity research of natural products are of great significance to human life and health. For example, humans have discovered antimalarial active molecules quinine and artemisinin in natural products, anti-tumor active molecule toxal, etc. in natural products. And chloroquine, artemether, eribulin, etc. developed on the basis of active natural products have greatly promoted the treatment research of related diseases, and provided an important guarantee for people's life and health. At the same time, as one of the important branches of organic chemistry, the total synthesis of natural products has also promoted the development of organic chemistry and other related disciplines.

High-tension structures are ubiquitous in natural products, leading to the unique biological activity of natural products. The trans 5/5 fused ring structure is one of the representatives of high-tension structures. Although the number of natural products with trans 5/5 fused ring is limited in nature, the unique activity and high synthesis challenges of this type of natural products have attracted the attention of scientists. However, due to the high difficulty of synthesis, there are few reports on the synthesis of trans 5/5 fused rings. These factors limit the research on the activity of natural products containing this type of structure.

The research goal of this thesis is that the natural product β-funebrene containing high-tension trans 5/5 fused ring is one of the representatives. In the course of the research, this paper first briefly summarizes the synthesis strategies of trans 5/5 fused rings that have been reported so far. On this basis, taking the intramolecular [3+2] cyclization reaction developed by the research group as the core strategy, a trans 5/5 cyclization was constructed in one step. Subsequently, the six-membered ring was successfully constructed by the aldol reaction, and the total synthesis of the natural product β-funebrene was realized after two steps of functional group transformation, which provided a material basis for further activity research.

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