Total synthesis of prostaglandin A2 involving the reaction of a heterocuprate reagent with an allyl epoxide

Chapleo, Christopher B.; Finch, Mark A. W.; Lee, Thomas V.; Roberts, Stanley M.; Newton, Roger F.

doi:10.1039/p19800002084

Cited by 17 publications

(5 citation statements)

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“…The active component was isolated by chromatographic separation. Spectroscopic analyses ( Figures S1–S3, Supplementary Materials ) revealed that the purified compound was identical to PGA 2 ( Figure 1 ) [ 13 , 14 , 15 ]. PGA 2 was recently independently isolated from the same genus of soft coral and shown to inhibit LPS-induced production of NO in RAW264.7 cells [ 16 ].…”

Section: Resultsmentioning

confidence: 99%

Inhibition of Lipopolysaccharide-Induced Inflammatory Signaling by Soft Coral-Derived Prostaglandin A2 in RAW264.7 Cells

et al. 2022

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Lipopolysaccharide (LPS) is a component of the outer membrane of Gram-negative bacteria and causes inflammatory diseases. We searched MeOH extracts of collected marine organisms for inhibitors of LPS-induced nitric oxide (NO) production in RAW264.7 cells and identified prostaglandin A2 (PGA2) as an active compound from the MeOH extract of the soft coral Lobophytum sp. PGA2 inhibited the production of NO and reduced the expression of inducible NO synthase (iNOS) in LPS-stimulated RAW264.7 cells. Although short preincubation with PGA2 did not inhibit LPS-induced degradation and resynthesis of IκBα, the suppressive effect of PGA2 was observed only after a prolonged incubation period prior to LPS treatment. In addition, PGA2-inhibited NO production was negated by the addition of the EP4 antagonist L161982. Thus, PGA2 was identified as an inhibitor of LPS-induced inflammatory signaling in RAW264.7 cells.

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Section: Resultsmentioning

confidence: 99%

Inhibition of Lipopolysaccharide-Induced Inflammatory Signaling by Soft Coral-Derived Prostaglandin A2 in RAW264.7 Cells

et al. 2022

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“…The synthesis of key cyclopentenol 9 proceeded straightforwardly from lactone 14 in a few additional steps. Thus, standard olefination of the aldehyde function reductively released from lactone 14 (DIBAL-H, DCM, −78 °C, 1 h, 96%) with the nonstabilized Wittig reagent prepared from Ph 3 P(CH 2 ) 4 COOH and t -BuOK in THF smoothly gave the corresponding Z olefin 15 in 84% yield . Methyl ester 9 was then obtained in 90% isolated yield by exposure of carboxylic acid 15 to ethereal solution of CH 2 N 2 .…”

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First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂

et al. 2003

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Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.

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“…To this aim the fully functionalized hydroxyacid 13 used in the Roberts synthesis of PGA 2 was prepared and subjected to the A-J swap. 13 Thus, compound 13 was first converted to the corresponding methyl ester and then exposed to o-nitrophenyl selenocyanate and Bu 3 P in THF.…”

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“…With an A−J swap protocol in hand we then turned our attention to the preparation of an advanced intermediate for the PGJ 2 synthesis (Scheme ). To this aim the fully functionalized hydroxyacid 13 used in the Roberts synthesis of PGA 2 was prepared and subjected to the A−J swap …”

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A → J Prostaglandin Swap: A New Tactic for Cyclopentenone Prostaglandin Synthesis

et al. 2003

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A practical methodology for the synthesis of J-type prostaglandins has been developed starting from the well-consolidated approaches established for the synthesis of A-type prostaglandins. An efficient 1,3-allylic transposition of the C-9 hydroxyl group of intermediate 4 furnished the advanced precursor 5 for J(2) synthesis. Our optimized A-J swap protocol employed selenium chemistry, involving the [2,3] sigmatropic rearrangement of secondary allylic selenoxide 11a.

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Total synthesis of prostaglandin A2 involving the reaction of a heterocuprate reagent with an allyl epoxide

Cited by 17 publications

References 0 publications

Inhibition of Lipopolysaccharide-Induced Inflammatory Signaling by Soft Coral-Derived Prostaglandin A2 in RAW264.7 Cells

Inhibition of Lipopolysaccharide-Induced Inflammatory Signaling by Soft Coral-Derived Prostaglandin A2 in RAW264.7 Cells

First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂

A → J Prostaglandin Swap: A New Tactic for Cyclopentenone Prostaglandin Synthesis

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Total synthesis of prostaglandin A2 involving the reaction of a heterocuprate reagent with an allyl epoxide

Cited by 17 publications

References 0 publications

Inhibition of Lipopolysaccharide-Induced Inflammatory Signaling by Soft Coral-Derived Prostaglandin A2 in RAW264.7 Cells

Inhibition of Lipopolysaccharide-Induced Inflammatory Signaling by Soft Coral-Derived Prostaglandin A2 in RAW264.7 Cells

First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2

A → J Prostaglandin Swap: A New Tactic for Cyclopentenone Prostaglandin Synthesis

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First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂