クアトリゲミンCとサイコラインのエナチオセレクティブ・トータル合成

Alec D Lebsack¹, J T Link, Larry E Overman

¹Department of Chemistry, 516 Rowland Hall, University of California Irvine, California 92697-2025, USA.

Journal of the American Chemical Society

|August 1, 2002

まとめ

クアトリゲミンCとサイコラインの最初の完全合成が達成されました. これらの複雑なポリピロリディノインドリンアルカロイドは,新しい合成戦略を使用して構築され,その構造を確認しました.

科学分野:

有機化学オーガニック・ケミストリー
トータル・シンセシス総合成
アルカロイド化学アルカロイド化学

背景:

ポリピロリディノインドリンアルカロイドは,複雑な自然製品のクラスを表しています.
これまでの合成の試みでは,このファミリーの上位階のメンバーにアクセスできませんでした.

研究の目的:

クアドリゲミンCとサイコラインの最初の総合合成を報告する.
複雑なポリピロリディノインドリンアルカロイドへの効率的な合成経路を開発する.

主な方法:

合成はオキシンドールとイサチンから派生したメソキモナンチンから始まった.
重要なステップには,スティルクロスカップリングと触媒非対称ヘックサイクリングが含まれています.
戦略は,ステレオセンターを設置するためにメソ前駆体デシンメトリゼーションを伴う.

主要な成果:

クアドリゲミンC (1) とサイコライン (3) を合成した.
クアドリゲミンCの合成は19つの線形ステップで完了し,全体の収量は2%でした.
62%の収量と90%のエナティオメール過剰で重要な中間物質が得られた.

結論:

トータル合成は,クアドリゲミンCの相対的および絶対的構成を厳密に確認しています.
開発された合成方法論は,より高次のポリピロリディノインドリンアルカロイドへのアクセスを提供します.

さらに関連する動画

08:31

Conscious and Non-conscious Representations of Emotional Faces in Asperger's Syndrome

Published on: July 31, 2016

09:38

Generalized Psychophysiological Interaction (PPI) Analysis of Memory Related Connectivity in Individuals at Genetic Risk for Alzheimer's Disease

Published on: November 14, 2017

関連する概念動画

00:49

Complementation Tests

A complementation test is a simple cross to identify whether the two mutations are located on the same gene or different genes. It was first performed by Edward Lewis in the 1940s while working on fruit flies. He developed the test to identify the location and arrangement of different mutations on chromosomes.
Organisms heterozygous for different mutations are crossed pairwise in all combinations. If present on different genes, the mutations can complement each other by providing the missing...

01:24

Defining Psychology

Psychology is the scientific discipline dedicated to understanding both observable behavior and the internal mental processes underlying such behavior. It aims to comprehend human nature and apply this understanding to solve practical problems, enhance well-being, and improve societal outcomes. An example of psychology's application is the study of prosocial behavior, such as why and under what conditions individuals might help strangers in need. This process involves describing observed...

01:30

Introduction to Biological Bases of Psychology

Biopsychology serves as a vital bridge connecting the intricate domains of biology and psychology, shedding light on how biological systems influence psychological phenomena. This field scrutinizes the biological substrates of behavior and mental processes, emphasizing the nervous system along with the roles of neurotransmitters, hormones, and genetics. It also incorporates evolutionary perspectives to explain the adaptive nature of mental functions.
The nervous system, the cornerstone of...

01:28

Adler's Individual Psychology

Alfred Adler, a prominent figure in psychology, founded the school of individual psychology. In contrast to Freud's emphasis on sexual or aggressive motives, Adler suggested that individuals are primarily motivated by their purposes and goals. He believed that people strive for perfection rather than pleasure. Adler argued that individuals could creatively act upon their genetic inheritance and environmental experiences to shape their own lives, emphasizing conscious motivation over unconscious...

01:24

Cattell's 16 Personality Factors

Raymond Cattell's trait theory offers a structured framework for understanding personality by distinguishing between two critical traits: surface and source traits. Surface traits are observable patterns of behavior, such as indecisiveness, anxiety, and irrational fears. These traits are less stable, varying across situations and over time. This means that they are less helpful in understanding the deeper aspects of an individual's personality.
In contrast, source traits are the fundamental,...

01:25

Beck's Cognitive Therapy

Cognitive therapy is a psychological approach designed to address distortions in thinking, which can lead to negative emotions and unrealistic beliefs. These cognitive distortions often influence how individuals interpret and respond to situations, exacerbating emotional distress. Below are some prevalent cognitive distortions, their characteristics, and examples of how they manifest in thought processes.
Arbitrary Inference
Arbitrary inference involves making conclusions without sufficient...

関連する実験動画