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Development of chiral building blocks having a bicyclo[3.3.0]octane framework using a diastereomeric resolution-selective deprotection. 2015

Masafumi Tamura, and Miki Oyamada, and Yoshiaki Shirataki
Faculty of Pharmaceutical Sciences, Josai University, Saitama, Japan.

A protocol is presented for an efficient and practical approach to the synthesis of enantiomerically pure bicyclo[3.3.0]octane derivatives from achiral Cs-symmetric bicyclo[3.3.0]octane-2,8-dione using a diastereomeric resolution-selective deprotection method. This method affords chiral building blocks having bicyclo[3.3.0]octane framework with the same site of diastereotopic carbonyl functional group.

UI MeSH Term Description Entries
D009795 Octanes Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Isooctanes
D001643 Bridged Bicyclo Compounds Saturated alicyclic hydrocarbon molecules consisting of two rings that have two non-adjacent atoms in common. Bicyclo Compounds,Bicyclo Compounds, Bridged
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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