Journal of the American Chemical Society · 1969 · 572 citations · 0 references
Life SciencesBiochemistryMedicinal ChemistryHormone BiochemistryNatural Product BiosynthesisSteroid BiochemistryHormone BiosynthesisHormone SynthesisOrganic SynthesisRetrosynthetic AnalysisSteroid BiosynthesisSteroid Hormone BiochemistryPrecursor ChemistryPrecursor SelectionProstaglandin AnaloguesProstaglandin E2 BiosynthesisProstaglandin F2alpha BiosynthesisStereochemistry Of Steroid HormonesStereocontrolled Library Synthesis
A new approach to the synthesis of prostaglandins, designed with the following objectives in mind, is reported. The objectives were: 1) control of stereochemistry; 2) the synthesis of all of the primary prostaglandins and a variety of analogs from a single precursor; and 3) optical resolution at an early stage. The fifteenth synthesis step yielded dl-prostaglandin F2 alpha identical to the natural hormone. Step by step routes of synthesis and stereochemistry are depicted in the text.