Formal total synthesis of RK-397 via an asymmetric hydration and iterative allylation strategy.
A formal total synthesis of the oxopentaene macrolide antibiotic RK-397 has been achieved. Nine stereocenters were established by a combination of allylation and our asymmetric hydration reactions and a 1,5 anti-selective aldol reaction. The synthesis proceeded in 19 steps from simple achiral conjugated dienoates.
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Haibing
H
Guo
Matthew S
MS
Mortensen
George A
GA
O'Doherty
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D018942:Macrolides; C084367:RK 397