Total Syntheses of (±)-Rhodonoids C, D, E, F, and G and Ranhuadujuanine B
Hao Wu1, Richard P Hsung2, Yu Tang1,3,4
1School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, P. R. China.
Organic Letters
|June 13, 2017
Summary
This study presents novel synthetic routes for complex natural products, rhodonoids C-G and ranhuadujuanine B. Key steps involved chromene construction and biomimetic cyclization, enabling access to these challenging molecular architectures.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Natural products like rhodonoids and ranhuadujuanine B possess complex structures with potential biological activities.
- Efficient and scalable synthetic strategies are crucial for accessing these compounds for further study.
Purpose of the Study:
- To develop divergent, biosynthetically inspired synthetic pathways for (±)-rhodonoids C-G and (±)-ranhuadujuanine B.
- To establish key chemical transformations for constructing the core scaffolds of these natural products.
Main Methods:
- Formal oxa-[3 + 3] annulation for chromene unit construction.
- Biomimetic acid-catalyzed intramolecular cyclization.
- Cationic [2 + 2] cycloaddition for cyclobutane core formation.
Main Results:
- Successful synthesis of (±)-rhodonoids C-G and (±)-ranhuadujuanine B.
- Demonstration of a convergent synthetic strategy.
- Establishment of key bond-forming reactions for complex natural product synthesis.
Conclusions:
- The developed synthetic routes provide access to valuable natural products.
- The employed methodologies highlight the power of biomimetic strategies in organic synthesis.
- This work contributes to the field of total synthesis and natural product chemistry.
More Related Videos
Related Concept Videos
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.8K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.8K
01:25Antianginal Drugs: Calcium Channel Blockers and Ranolazine
1.6K
Angina pectoris, a primary symptom of ischemic heart disease, requires careful pharmacological interventions. In this context, calcium channel blockers (CCBs) and ranolazine have emerged as crucial pharmacotherapeutic agents, providing deep insights into the complexities of angina management.
CCBs, a diverse class that includes dihydropyridines (nifedipine) and diphenylalkylamines (verapamil and diltiazem), exert their effect by blocking calcium channels in cardiac and smooth muscle cells. This...
CCBs, a diverse class that includes dihydropyridines (nifedipine) and diphenylalkylamines (verapamil and diltiazem), exert their effect by blocking calcium channels in cardiac and smooth muscle cells. This...
1.6K
01:33Radical Halogenation: Stereochemistry
4.7K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
Halogenation to form a new chiral center:
4.7K
01:27Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
3.0K
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).
3.0K
02:33Stereoisomerism of Cyclic Compounds
11.4K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
11.4K
01:28Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
5.2K
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.
5.2K