title: Stereoselective synthesis of rapamycin fragment to build a macrocyclic toolbox.
abstract: A stereoselective synthesis of a rapamycin fragment is developed and further utilized toward building a macrocyclic chemical toolbox. The amino alcohol moiety embedded in the 22-membered macrocyclic ring allowed for the addition of a variation in the chiral side chain. The key reactions leading to the synthesis of the rapamycin-derived pyran fragment include the following: (i) Paterson aldol, (ii) stereoselective β-OH carbonyl reduction, and (iii) regio- and stereoselective intramolecular oxy-Michael reaction. The other piece needed for building the macrocyclic diversity was obtained from the coupling of various amino alcohol moieties with S-pipecolic acid.
authors.affiliation: Dr. Reddy's Institute of Life Sciences (DRILS), University of Hyderabad Campus , Hyderabad 500046, India.
authors.forename: Shiva Krishna Reddy
authors.initials: SK
authors.lastname: Guduru
authors.forename: Ravikumar
authors.initials: R
authors.lastname: Jimmidi
authors.forename: Girdhar Singh
authors.initials: GS
authors.lastname: Deora
authors.forename: Prabhat
authors.initials: P
authors.lastname: Arya
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry; D020123:Sirolimus / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D010875:Pipecolic Acids; D011714:Pyrans; D020123:Sirolimus