Hydrolytic Kinetic Resolution as an Emerging Tool in the Synthesis of Bioactive Molecules.

A variety of racemic epoxides mainly derived from terminal olefins, such as aliphatic epoxides, multifunctionalized epoxides and amine-substituted epoxides, have been successfully resolved into the enantiomerically pure epoxides and diols using �Jacobsen’s hydrolytic kinetic resolution (HKR) method. The chiral epoxides thus prepared were further elaborated by synthetic manipulation to provide a variety of compounds of biological interest. A general synthetic strategy for the construction of <italic>syn</italic>/<italic>anti</italic>-1,3-polyol systems using iterative HKR has been developed, which was subsequently utilized in the synthesis of natural products with a broad range of biological activity. The protocol for the 1,3-polyols was also further extended to the synthesis of 1,3-amino alcohols. 1 Introduction 2 Aliphatic/Aromatic Epoxides 2.1 Synthesis of (<italic>R</italic>)- and (<italic>S</italic>)-Massoialactone 2.2 Synthesis of Iso-cladospolide B and Cladospolide B 2.3 Synthesis of Herbarumin III 2.4 Synthesis of Decarestrictine D 2.5 Concise Synthesis of (-)-Deoxoprosopinine 2.6 Synthesis of <italic>cis</italic>-Lauthisan 2.7 Synthesis of CMI-977 (LDP-977) 2.8 Synthesis of (<italic>S</italic>)-Betaxolol and (<italic>S</italic>)-Metoprolol 2.9 Synthesis of (<italic>S</italic>)-Vigabatrin and (<italic>S</italic>)-Dihydrokavain 3 Multifunctionalized Epoxides 3.1 Synthesis of (+)-Boronolide 4 Amine-Substituted Epoxides 4.1 Synthesis of Protected (2<bold></bold><italic>R</italic>,4<italic>S</italic><bold></bold>)-4-Hydroxyornithine 5 Development of a General Synthetic Strategy for the Construction of 1,3-Polyols 6 Synthesis of Compounds Containing 1,3-Polyols and Amino Alcohols 6.1 Synthesis of Tarchonanthuslactone and Cryptocarya Diacetate 6.2 Synthesis of Strictifolione 6.3 Synthesis of the Lactone Moiety of Compactin 6.4 Synthesis of Verbalactone 6.5 Synthesis of Tetrahydrolipstatin 6.6 Synthesis of Decarestrictine J 6.7 Construction of a 1,3-Amino Alcohol: Application to the Synthesis of (+)-Negamycin 7 Conclusion [ABSTRACT FROM AUTHOR]