The first total synthesis of dragmacidin d

Neil K Garg1, Richmond Sarpong, Brian M Stoltz

  • 1The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 164-30, Pasadena, California 91125, USA.

Related Concept Videos

Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
[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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Otto and Diesel Cycle01:27

Otto and Diesel Cycle

An Otto engine is a four-stroke engine that uses a mixture of gasoline and air as the working fuel. The fuel is injected into the cylinder, and the piston is moved completely down so that the cylinder is at maximum volume. By moving the piston up, adiabatic compression takes place. The spark plug ignites the gasoline-air mixture, and the burning fuel adds heat to the system at a constant volume. The heated mixture expands adiabatically and gets further cooled by exhausting heat, and this cyclic...
Brick Masonry01:12

Brick Masonry

Brick masonry uses bricks as the building blocks and involves building walls from individual bricks laid in mortar. The basic building block of brick masonry is the wythe, a vertical layer of bricks with a thickness of one brick. Within a wythe, bricks can be laid in various courses or patterns, with the most common being the stretcher course, where bricks are laid with their long edge horizontal and face parallel to the wall.
For thicker walls, multiple wythes are bonded together using...