(-) - 默西卡尔宾的总合成
Rie Nakajima1, Tsuyoshi Ogino, Satoshi Yokoshima
1Graduate School of Pharmaceutical Sciences, University of Tokyo,7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society
|January 9, 2010
概括
在10个步骤中成功完成了 (-) - 默西卡尔的总合成. 这项研究使用先进的合成有机化学方法证实了该分子的结构和绝对配置.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- (-) - 默西卡是一种复杂的天然产品,具有具有挑战性的分子结构.
- 以前的合成路线可能在效率或立体化学控制方面存在局限性.
研究的目的:
- 为了实现第一个 (-) - - 默西卡尔宾的全合成.
- 通过合成来证实 (-) - 默西卡的拟议结构和绝对配置.
主要方法:
- 用于基合成的埃申莫塞尔-塔纳贝型碎片化.
- 索诺加希拉合和金 ((III) 催化循环用于内骨架结构.
- 一个的过程,用于组装循环 imine 和 hemiaminal 功能.
主要成果:
- 从已知的基托中完成了 (-) - 默西卡尔宾的10步全合成.
- 合成成功生成了一种带有四等碳中心的基因.
- 基核被高效地构建,关键的功能部分被组装在一个一个的程序.
结论:
- 总合成毫不含糊地证实了报告中的 (-) - 默西卡尔的结构和绝对配置.
- 开发的合成策略为这种复杂的化物提供了一条有效的途径.
相关概念视频
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Oxymercuration-Reduction of Alkenes
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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.


