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• W2318082511 abstract "In this paper we describe a novel general synthetic approach to B1- and L1-type phytoprostanes, which are formed in vivo from free-radical-catalyzed nonenzymatic peroxidation of α-linolenic acid (1). The synthesis of phytoprostanes (RS)-9-L1-PhytoP (5), (R)-9-L1-PhytoP (5a), (RS)-16-B1-PhytoP (6), and (RS)-16-L1-PhytoP (7) exemplifies this strategy. The common starting compound 8 has been proved to be synthetically equivalent to a cyclopent-2-en-1-one synthon having opposite donor and acceptor properties at carbons α and β, respectively. Key steps include the chemoselective lithiation of a 1-iodo-2-bromoolefin, the introduction of the side chains by transition-metal catalysis following Heck- or Suzuki-type protocols, the construction of an enone moiety by a mild Au(I)-catalyzed Meyer Schuster rearrangement, and a lipase-mediated hydrolysis of methyl esters to deliver the phytoprostanes as free carboxylic acids." @default.
• W2318082511 created "2016-06-24" @default.
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• W2318082511 date "2015-01-26" @default.
• W2318082511 modified "2023-09-25" @default.
• W2318082511 title "General Strategy for the Synthesis of B₁ and L₁ Prostanoids: Synthesis of Phytoprostanes (<i>RS</i>)-9-L₁-PhytoP, (<i>R</i>)-9-L₁-PhytoP, (<i>RS</i>)-16-B₁-PhytoP, and (<i>RS</i>)-16-L₁-PhytoP" @default.
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• W2318082511 doi "https://doi.org/10.1021/jo502538b" @default.
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