Short Route to Platencin

The synthesis of the complex tricyclic core of the terpenoid antibiotic platencin is achieved in a concise, protecting group-free and stereoselective manner. A flexible approach that highlights the intramolecular aldol reaction as the key step toward the construction of the bicyclo[2,2,2]octane ring...

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Bibliographic Details
Published in:Organic letters 2013-07, Vol.15 (14), p.3782-3785
Main Authors: Yadav, J. S, Goreti, Rajendar, Pabbaraja, Srihari, Sridhar, B
Format: Article
Language:English
Subjects:
Aminophenols - chemical synthesis
Aminophenols - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Bridged Bicyclo Compounds - chemistry
Cyclization
Molecular Structure
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Stereoisomerism
Terpenes - chemical synthesis
Terpenes - chemistry
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Summary:The synthesis of the complex tricyclic core of the terpenoid antibiotic platencin is achieved in a concise, protecting group-free and stereoselective manner. A flexible approach that highlights the intramolecular aldol reaction as the key step toward the construction of the bicyclo[2,2,2]octane ring from an angular allyl decalone in both the trans-fused and the cis-fused forms is demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401760e