title: Synthesis of Enantiomerically Pure Stereomers of Rosaprostol.
abstract: Enantiopure stereomers of rosaprostol 1, an antiulcer drug, were synthesized from diastereomeric building blocks (-)-5a and (+)-5b. Conversion of (-)-5a into rosaprostol stereomer (-)-(1S,2R,5R)-1a was accomplished in nine steps in 18% overall yield. In this sequence, fully diastereoselective hydrogeneration of the endocyclic carbon double bond in the cyclopentenone ring was key, generating a new stereogenic center (C-2 in 1a). C-5 epimeric rosaprostol (-)-(1S,2R,5S)-1b was obtained from (-)-1a in 72% yield by a two-reaction sequence involving methylation and one-pot Mitsunobu esterification-hydrolysis.
authors.affiliation: Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences , Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Beata
authors.initials: B
authors.lastname: Łukasik
authors.affiliation: Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences , Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Wiesława
authors.initials: W
authors.lastname: Perlikowska
authors.affiliation: Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences , Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Remigiusz
authors.initials: R
authors.lastname: Żurawiński
authors.affiliation: Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences , Sienkiewicza 112, 90-363 Łódź, Poland.
authors.forename: Marian
authors.initials: M
authors.lastname: Mikołajczyk
mesh_terms: D004951:Esterification; D006868:Hydrolysis; D015394:Molecular Structure; D011466:Prostanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011466:Prostanoic Acids; C035288:rosaprostol