139278-19-6Relevant articles and documents
Modular Synthesis of Diverse Natural Product-Like Macrocycles: Discovery of Hits with Antimycobacterial Activity
Dow, Mark,Marchetti, Francesco,Abrahams, Katherine A.,Vaz, Luis,Besra, Gurdyal S.,Warriner, Stuart,Nelson, Adam
, p. 7207 - 7211 (2017/05/31)
A modular synthetic approach was developed in which variation of the triplets of building blocks used enabled systematic variation of the macrocyclic scaffolds prepared. The approach was demonstrated in the synthesis of 17 diverse natural product-like macrocyclic scaffolds of varied (12–20-membered) ring size. The biological relevance of the chemical space explored was demonstrated through the discovery of a series of macrocycles with significant antimycobacterial activity.
Total synthesis of (+)-A83543A [(+)-lepicidin A]
Evans, Darid A.,Cameron Black
, p. 4497 - 4513 (2007/10/02)
The first synthesis of the macrolide insecticide A83543A (lepicidin A) has been completed using a Diels-Alder strategy to construct the carbocyclic framework. Diene synthesis through Pd-catalyzed Stille coupling of a macrocyclic vinylstannane and suitably functionalized vinyl iodide was followed by a diastereoselective Lewis acid-mediated intramolecular Diels-Alder reaction to construct the trans hydrindene subunit. Refunctionalization and intramolecular aldol condensation afforded the differentially protected (+)-lepicidin A aglycon. Successive glycosidations with 2,3,4-tri-O-methyl-D-rhamnose and N-protected L-forosamine followed by deprotection and methylation completed the synthesis of the enantiomer of the natural product.
