Access to Enantiopure 4-Substituted 1,5-Aminoalcohols from Phenylglycinol-Derived δ-Lactams: Synthesis of Haliclona Alkaloids

LiNH2BH3-promoted reductive opening of 8-substituted phenylglycinol-derived oxazolopiperidone lactams leads to enantiopure 4-substituted-5-aminopentanols, which are used as starting building blocks in the synthesis of the Haliclona alkaloids haliclorensin C, haliclorensin, and halitulin (formal). The starting lactams are easily accessible by a cyclocondensation reaction of (R)-phenylglycinol with racemic gamma-subtituted delta-oxoesters, in a process that involves a dynamic kinetic resolution.