Application of the intramolecular Yamamoto vinylogous aldol reaction to the synthesis of macrolides.
An intramolecular version of the Yamamoto vinylogous aldol reaction, a method that employs the bulky Lewis acid ATPH to control the site of aldolization, is described. This macrocyclization process is effective for the construction of 10-, 12-, and 14-membered macrolides. The yields are high (70-90%), and the reaction can proceed with excellent remote stereocontrol (dr > or = 20:1) with chiral substrates.
Abramite
Joseph A
JA
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Sammakia
Tarek
T
D018360:Crystallography, X-Ray; D018942:Macrolides / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure
D018942:Macrolides