A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity.
A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of α/β- and d/l-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.
Department of Chemistry & Biochemistry, The University ofTexas at Austin, 1 University Station A5300, Austin, Texas 78712, United States.
Svetlana A
SA
Borisova
Sanjeeva R
SR
Guppi
Hak Joong
HJ
Kim
Bulan
B
Wu
John H
JH
Penn
Hung-Wen
HW
Liu
George A
GA
O'Doherty
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006031:Glycosylation; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000900:Anti-Bacterial Agents; D018942:Macrolides; C008517:methymycin; D010165:Palladium