AI Article Synopsis
- - The total synthesis of lundurines A-C has been successfully achieved in both racemic (mixed) and enantiopure (single form) variations in 11-13 and 12-14 steps, respectively.
- - This synthesis was performed without the need for protection or deprotection of functional groups, simplifying the process.
- - Key techniques used included a new tandem double condensation/Claisen rearrangement, gold(I)-catalyzed alkyne hydroarylation, cyclopropanation through a [3 + 2] cycloaddition, and a unique olefin migration method that enhances efficiency in the final stages.
Article Abstract
The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4819460 | PMC |
| http://dx.doi.org/10.1021/jacs.6b01428 | DOI Listing |
Publication Analysis
Top Keywords
total synthesis
8
synthesis lundurines
8
lundurines a-c
8
concise total
4
a-c enabled
4
enabled gold
4
gold catalysis
4
catalysis homodienyl
4
homodienyl retro-ene/ene
4
retro-ene/ene isomerization
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!