Direct Entry to 4,10-Didesmethyl (9S)-Dihydroerythronolide A via Catalytic Allene Osmylation.
Desmethyl erythronolides have emerged as macrolide targets that may prove effective against resistant bacteria. A five-step sequence to 4,10-didesmethyl (9S)-dihydroerythronolide A (1) from known cyclic bis[allene] 13 is reported. Key structural and mechanistic aspects of the synthesis are discussed along with catalytic allene osmylation. An improved route to 13 is also described.
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Libing
L
Yu
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Huan
H
Wang
Department of Chemistry, West Virginia University , 406 Clark Hall, Prospect Street, Morgantown, West Virginia 26506, United States.
Novruz G
NG
Akhmedov
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Christopher
C
Sowa
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Kai
K
Liu
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Hiyun
H
Kim
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
Lawrence
L
Williams
D000466:Alkadienes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism
D000466:Alkadienes; D000900:Anti-Bacterial Agents; C038316:erythronolide A; C025947:propadiene; D004917:Erythromycin