通过受控的寡合化,对烯合成酶抑制剂萨拉戈西克酸C进行自相一致的合成
David A Nicewicz1, Andrew D Satterfield, Daniel C Schmitt
1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Journal of the American Chemical Society
|December 5, 2008
概括
研究人员开发了一种新的方法,用于使用silyl glyoxylates进行立体控制的寡合化. 这种方法有效地构建复杂的碳骨架,以合成素合成酶抑制剂萨拉戈西克酸C为例.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 自然产品的合成自然产品的合成
背景情况:
- 状的自然产品通常具有重复的子单元,但用于骨架结构的受控寡合化仍然不发达.
- 斯夸伦合成酶抑制剂是重要的治疗点,萨拉戈西克酸C就是一个值得注意的例子.
研究的目的:
- 引入一种新的,立体控制的寡合化策略,用于构建复杂的碳框架.
- 为了证明在这个过程中silyl glyoxylates作为甘油酸合成子的实用性.
- 为了高效地合成萨拉戈西克酸C的碳骨架.
主要方法:
- 使用西基氧酸盐作为双极糖醇酸合成剂.
- 在碳骨架框架结构中采用受控的寡合化反应.
- 应用了这种方法来合成萨拉戈西克酸C.
主要成果:
- 实现了碳骨架的快速和立体控制的形成.
- 该方法提供了一个理想的保护集团计划.
- 将功能组修复和氧化状态操纵的需要降至最低.
结论:
- 开发了一个新的,有效的策略,用于立体控制的寡合化.
- 基氧酸是构建复杂分子的有效合成子.
- 这种方法简化了天然产品的合成,如萨拉戈西克酸C.
相关概念视频
Ziegler–Natta Chain-Growth Polymerization: Overview
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...
Cationic Chain-Growth Polymerization: Mechanism
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Radical Chain-Growth Polymerization: Mechanism
The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...
Anionic Chain-Growth Polymerization: Mechanism
The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael acceptor.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

