title: Biomimetic Total Synthesis of (-)-Penibruguieramine A Using Memory of Chirality and Dynamic Kinetic Resolution.
abstract: The fully stereocontrolled total synthesis of (-)-penibruguieramine A, a naturally occurring marine pyrrolizidine alkaloid, is described in this study for the first time. The key synthetic sequence is the biomimetic aldol reaction of the proline pentaketide amide. The principles of "memory of chirality" (MOC) and "dynamic kinetic resolution" (DKR) are applied to this reaction for the asymmetric synthesis using proline as the only chiral source. A mechanistic rationale is discussed for the excellent stereochemical outcome in a protic solvent environment.
authors.affiliation: College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742 (Korea).
authors.forename: Jae Hyun
authors.initials: JH
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742 (Korea).
authors.forename: Seokwoo
authors.initials: S
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742 (Korea). pennkim@snu.ac.kr.
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
mesh_terms: D032701:Biomimetics; D007700:Kinetics; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011763:Pyrrolizidine Alkaloids; C000588723:penibruguieramine A
keywords: aldol reaction; biomimetic synthesis; dynamic kinetic resolution; memory of chirality; total synthesis