Chemical Transformations of 9,11-Ethano-13,15-isoxazolinoprostanoids

Chemical transformations of 9,11-ethano-13,15-isoxazolinoprostanoids furnished new prostanoids with a bufunctional fragment of β-hydroxyketone and γ-aminoalcohol in the ω-chain. The reaction of β-hydroxyketones with methanesulfonyl chloride gave rise to prostanoids with an enone component in the ω-chain. 9,11-Ethano-16-thiaprostanoids were prepared for the first time by nucleophilic addition of thiols to the polarized double bond in the ω-chain. The 1,3-dipolar addition to terminal alkenes of nitrile oxides generated from nitromethylene derivatives of bicycloheptane provided 9,11-ethano-13,15-isoxazolinoprostanoids with an alkyl, phenyl, or additional heterocyclic fragment in the ω-chain.