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Beilstein J. Org. Chem. 2016, 12, 2234–2239, doi:10.3762/bjoc.12.215
Graphical Abstract
Figure 1: Structure of rosaprostol (1) and numbering system.
Figure 2: The structures of stereoisomers of rosaprostol (1).
Scheme 1: Synthesis of stereoisomeric rosaprostols 1a and 1b from (−)-2a.
Scheme 2: Synthesis of racemic rosaprostol (±-1).
Scheme 3: Resolution of racemic cyclopentanone 3. Reagents and conditions: (a) Al2O3, SiO2, MS 5 Å, DCM, rt, ...
Scheme 4: Synthesis of rosaprostol stereoisomers 1a and 1c. Reagents and conditions: (a) KOH/Al2O3, OHC(CH2)5...
Scheme 5: Conversion of methyl ester (+)-6 into rosaprostol (−)-1a. Reagents and conditions: (a) L-Selectride...
Scheme 6: Synthesis of rosaprostol stereoisomers 1b and 1d. Reagents and conditions: (a) CH2N2, Et2O, −30 °C;...