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

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.8K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.8K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
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.
3.9K
Prochirality02:05

Prochirality

3.8K
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...
3.8K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.2K
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).
2.2K

You might also read

Related Articles

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

Sort by
Same author

[3 + 2] Cycloaddition of Iminyl Radicals and 2-Azaallyl Anions for the Synthesis of Multisubstituted 2-Imidazolines.

Organic letters·2026
Same author

Electrochemically driven strain-release dearomative (3 + 2) cyclization for the synthesis of bicyclo[2.1.1]hexane-fused polycyclic spiroindolines.

Chemical science·2026
Same author

Enantioselective Total Syntheses of Grayanoid (-)-Mollfoliagein A and (-)-Rhodomollein XXV.

Journal of the American Chemical Society·2026
Same author

Collective Total Synthesis of <i>Ergot</i> Alkaloids.

Organic letters·2026
Same author

Synthesis of Spirocyclohexadienones with Diverse Structural Types and Ring Sizes.

JACS Au·2026
Same author

Regioselective 1,2-Hydrogen Atom Transfer of N-Centered Radicals for C(sp<sup>3</sup>)-C(sp<sup>3</sup>) Coupling to Generate 1,2-Diamine Derivatives.

Organic letters·2026

Related Experiment Video

Updated: Jul 10, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
09:56

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

6.8K

Structure-Unit-Based Total Synthesis of (-)-Sinulochmodin C.

Yi-Peng Zhang1, Shufei Du1, Ying Ma1

  • 1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research and Development of Natural Products, Yunnan Characteristic Plant Extraction Laboratory, School of Pharmacy, Yunnan University, Kunming, 650091, P. R. China.

Angewandte Chemie (International Ed. in English)
|November 27, 2023
PubMed
Summary

Researchers achieved the first asymmetric total synthesis of sinulochmodin C, a complex norcembranoid diterpenoid. This synthesis utilized a novel structure-unit-based approach to construct its unique tetracyclic skeleton and strained ether bridge.

Keywords:
CyclizationNatural ProductsNorcembranoid DiterpenoidsOxa-Michael AdditionTotal Synthesis

More Related Videos

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
10:22

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer

Published on: November 30, 2020

3.5K
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.5K

Related Experiment Videos

Last Updated: Jul 10, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
09:56

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

Published on: September 6, 2019

6.8K
Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
10:22

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer

Published on: November 30, 2020

3.5K
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.5K

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Sinulochmodin C is a norcembranoid diterpenoid featuring a complex tetracyclic structure.
  • The molecule possesses a strained β-keto tetrahydrofuran moiety with a transannular ether bridge, presenting significant synthetic challenges.

Purpose of the Study:

  • To report the first structure-unit-based asymmetric total synthesis of sinulochmodin C.
  • To develop a synthetic strategy for constructing the intricate [7,6,5,5] tetracyclic skeleton and the strained ether bridge.

Main Methods:

  • Stereoselective construction of the tetracyclic core via an intramolecular double Michael addition.
  • Establishment of the γ-keto enone intermediate using vinylogous hydroxylation/oxidation or epoxide opening/oxidation.
  • Formation of the β-keto tetrahydrofuran moiety through Lewis/Brønsted acid-catalyzed transannular oxa-Michael addition.
  • Stereochemical inversion at C1 using Mukaiyama hydration and Pd-C hydrogenation.
  • Bioinspired transformation of sinulochmodin C into scabrolide A.

Main Results:

  • Successful asymmetric total synthesis of sinulochmodin C.
  • Stereospecific construction of the [7,6,5,5] tetracyclic skeleton.
  • Efficient formation of the transannular strained ether bridge and β-keto tetrahydrofuran moiety.
  • Demonstration of a bioinspired conversion to scabrolide A.

Conclusions:

  • The developed synthetic route provides access to sinulochmodin C and related norcembranoid diterpenoids.
  • This synthesis showcases a versatile strategy for assembling complex polycyclic natural products.
  • The study highlights the potential for bioinspired transformations in natural product chemistry.