Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.6K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.6K
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

1.2K
When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1.2K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

2.9K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
2.9K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.8K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.8K
Prochirality02:05

Prochirality

3.9K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
3.9K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

3.6K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.6K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Comprehensive multi-omics analyses elucidate the mechanism of male sexual dysfunction induced by chronic prostatitis/chronic pelvic pain syndrome in the experimental autoimmune prostatitis rat model.

The journal of sexual medicine·2026
Same author

3D printed trichome-inspired permeable bioadhesive for wearable bioelectronics.

Biofabrication·2026
Same author

Farnesoid X receptor and nuclear factor erythroid 2-related factor 2 synergistically ameliorate cholestatic liver injury by coordinating bile acid metabolism and transport.

Chemico-biological interactions·2026
Same author

Single-cell RNA sequencing reveals mucosal BPIFA1-high-expressing neutrophils aid immune defense in SARS-CoV-2 breakthrough infection.

The Journal of infectious diseases·2026
Same author

Trilobatin is associated with reduced lipid accumulation in multiple biological models: insights from transcriptomics, molecular docking, and molecular dynamics simulations.

Naunyn-Schmiedeberg's archives of pharmacology·2026
Same author

Breathable, Stretchable Electroporation Patches for Drug Delivery.

Small (Weinheim an der Bergstrasse, Germany)·2026

Related Experiment Video

Updated: Sep 12, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.1K

Total Synthesis of (+)-Pierisketone B.

Qi Gu1, Grant D Walby1, Michael D Wood1

  • 1Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, United States.

Journal of the American Chemical Society
|August 6, 2025
PubMed
Summary

The first total synthesis of (+)-pierisketone B, a complex diterpene, was achieved. This study details novel synthetic strategies for constructing its unique tetracyclic framework and stereocenters.

More Related Videos

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.9K
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

7.0K

Related Experiment Videos

Last Updated: Sep 12, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.1K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.9K
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

7.0K

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • (+)-Pierisketone B is a bioactive diterpenoid.
  • It features a complex 7/5/6/5 tetracyclic carbocyclic framework with multiple stereocenters.

Purpose of the Study:

  • To report the first total synthesis of (+)-pierisketone B.
  • To develop novel synthetic methodologies for constructing complex carbocyclic frameworks.

Main Methods:

  • Pauson-Khand cyclization to form the tricyclic core.
  • Hydroxyl-directed hydrogenation for the cis-fused hydrindanone moiety.
  • Mukaiyama aldol reaction and vinyl anion addition for A-ring formation.

Main Results:

  • Successful total synthesis of (+)-pierisketone B.
  • Construction of the intricate tetracyclic framework with numerous stereocenters, including two quaternary and five contiguous ones.
  • A 20-step longest linear sequence from (-)-linalool.

Conclusions:

  • The developed synthetic route is efficient for accessing (+)-pierisketone B.
  • The study showcases innovative applications of key reactions in complex molecule synthesis.