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Biomimetic Total Synthesis of (−)‐Penibruguieramine A Using Memory of Chirality and Dynamic Kinetic Resolution
Author(s) -
Kim Jae Hyun,
Lee Seokwoo,
Kim Sanghee
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504954
Subject(s) - kinetic resolution , chirality (physics) , chemistry , total synthesis , aldol reaction , pyrrolizidine , amide , stereochemistry , dynamic covalent chemistry , proline , enantioselective synthesis , combinatorial chemistry , computational chemistry , organic chemistry , molecule , amino acid , catalysis , physics , biochemistry , chiral symmetry breaking , supramolecular chemistry , quantum mechanics , quark , nambu–jona lasinio model
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.