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Updated: May 7, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

スピロサイクリックオキシンドールアルカロイドへの迅速なアクセス:パラジウムで触媒化された [3 + 2]トリメチレンメタンサイクロアディションの非対称性の適用

Barry M Trost, Dustin A Bringley, Ting Zhang

    Journal of the American Chemical Society
    |October 3, 2013
    PubMed
    まとめ

    研究者らは,マルクフォルティネスという,抗虫作用のある複雑な天然物質を合成した. この研究は,マークフォリンBの新合成経路とマークフォリンCの最初の非対称合成を詳細に説明し,重要なステレオセンターを確立しました.

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    Cycloaddition Reactions: Overview01:16

    Cycloaddition Reactions: Overview

    Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
    Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

    Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

    Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
    Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

    Cycloaddition Reactions: MO Requirements for Thermal Activation

    Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
    [4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

    [4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

    The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
    Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

    Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

    Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
    Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

    Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

    The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.