Prostaglandins. 2. Synthesis of prostaglandin F2.alpha. in optically active form from chiral precursors

Johnson, Francis; Paul, Kalidas; Favara, D.; Ciabatti, Romeo; Guzzi, U.

doi:10.1021/ja00372a015

Cited by 42 publications

(18 citation statements)

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“…The pure product was obtained as a yellow oil in 91 % yield. The spectroscopic and analytical data were identical to those reported by Flitsch et al9b…”

Section: Methodssupporting

confidence: 83%

Bis(oxazolinylmethyl) Derivatives of C₄H₄E Heterocycles (E = NH, O, S) as C₂‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

et al. 2009

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The synthesis of the three ligands employed in this study is based on the condensation of two molar equivalents of (S)-valinol with the diester precursors pyrrole-2,5-bis(ethyl)acetate (2a), furan-2,5-bis(ethyl)acetate (2b) and thiophene-2,5-bis(ethyl)acetate (2c). This gave the corresponding bis(oxazolinylmethyl)pyrrole (iPrL N H, 4a), bis(oxazolinylmethyl)-furan (iPrL O , 4b) and bis(oxazolinylmethyl)thiophene (iPrL S , 4c) ligands. Stirring 4a in MeOD at ambient temperature in the presence of a catalytic amount of acetic acid (1 mol-%) led to complete hydrogen/deuterium exchange in the two bridging methylene groups of the ligand. This behaviour is explained by an acetate-mediated reversible proton transfer between the oxazoline N atom and the methylene bridge, a conjecture which was supported by a DFT study of the process. Deprotonation of iPrL N H (4a) with tBuLi at -78°C and subsequent stirring with NiCl 2 yielded the square planar nickel(II) complex [Ni(iPrL N )Cl] (5). However, on stirring

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“…The pure product was obtained as a yellow oil in 91 % yield. The spectroscopic and analytical data were identical to those reported by Flitsch et al9b…”

Section: Methodssupporting

confidence: 83%

Bis(oxazolinylmethyl) Derivatives of C₄H₄E Heterocycles (E = NH, O, S) as C₂‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

et al. 2009

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“…The acetal intermediate 6 was synthesized from lutidine anion and 2-(2-bromoethyl)-l,3-dioxolane. This was deblocked to the aldehyde, which smoothly produced 2-methyl-6-(Z-4-nonenyl)pyridine (7) in a Wittig reaction (Johnson et al, 1982) with the phosphonium ylide (b) from 5-bromopentane. The olefin 7 was reduced, first with sodium in ethanol and then, after acidification to pH 6, by treatment with sodium cyanoborohydride to afford a mixture containing 2a and 2b (3.2: 1, respectively).…”

Section: Examination Of the Methylene Chloride Extracts Of Four Collementioning

confidence: 99%

Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico

et al. 1996

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A number of 15-carbon alkaloids have been identified in venom extracts of four Puerto Rican species of ants in the genusSolenopsis (Diplorhoptrum). Workers of a species from El Verde produced thecis andtrans isomers of 2-methyl-6-nonylpiperidine with the latter isomer predominating. The same compounds were identified in queens of a species from Río Grande, but in this species no alkaloids were detected in worker extracts. Workers of aDiplorhoptrum species collected on Mona Island produced primarily atrans-2-methyl-6-(Z-4-nonenyl)piperidine,3, with smaller amounts of thecis isomer, whereas the major compound found in the queens of the same species on Mona Island was (5Z,9Z)-3-hexyl-5-methylindolizidine, identical with the alkaloid produced by queens of a species collected on Cabo Rojo. Surprisingly, workers of the Cabo Rojo species produced (5Z,9Z)- and (5E,9E)-3-butyl-5-propylindolizidine (4 and5, respectively) reported earlier as the 223AB indolizidines from skins of dendrobatid frogs. The possible significance of the qualitative and quantitative differences in the venom alkaloids synthesized by queens and workers is discussed as is the possibility that ants containing such alkaloids may serve as a dietary source for the skin alkaloids used by certain frogs in chemical defense.

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“…A chiral synthesis of this compound from (S)-malic acid (127) has now been reported (168). A chiral synthesis of this compound from (S)-malic acid (127) has now been reported (168).…”

Section: Prostaglandinsmentioning

confidence: 99%

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

Scott

1984

Asymmetric Synthesis

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Prostaglandins. 2. Synthesis of prostaglandin F2.alpha. in optically active form from chiral precursors

Cited by 42 publications

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Bis(oxazolinylmethyl) Derivatives of C₄H₄E Heterocycles (E = NH, O, S) as C₂‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

Bis(oxazolinylmethyl) Derivatives of C₄H₄E Heterocycles (E = NH, O, S) as C₂‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

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Prostaglandins. 2. Synthesis of prostaglandin F2.alpha. in optically active form from chiral precursors

Cited by 42 publications

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Bis(oxazolinylmethyl) Derivatives of C4H4E Heterocycles (E = NH, O, S) as C2‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

Bis(oxazolinylmethyl) Derivatives of C4H4E Heterocycles (E = NH, O, S) as C2‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico

Readily Available Chiral Carbon Fragments and Their Use in Synthesis

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Bis(oxazolinylmethyl) Derivatives of C₄H₄E Heterocycles (E = NH, O, S) as C₂‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium

Bis(oxazolinylmethyl) Derivatives of C₄H₄E Heterocycles (E = NH, O, S) as C₂‐Chiral Meridionally Coordinating Ligands for Nickel and Chromium