• Title/Summary/Keyword: Stereogenic center

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A New Asymmetric Photoisomerization of 2,3-Dihydropyrrolo[1,2-b]benzisothiazole 5,5-Dioxides (2,3-Dihydropyrrolo[1,2-b]benzisothiazole 5,5-Dioxide들의 비대칭성 광이성질화 반응)

  • Elghamry, Ibrahim;Dopp, Dietrich
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.727-730
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    • 2010
  • A tricyclic ring system bearing new stereogenic center namely 2,3-dihydro[1]benzothieno[3,2-b]pyrrole 4,4-dioxide was synthesized by asymmetric photoisomerization of 2,3-dihydropyrrolo[1,2-b]benzisothiazole 5,5-dioxide by irradiation with 245 nm emission of the low-pressure mercury lamp. The chemical structure and the purity of the photoproduct were delineated preliminarily by IR, NMR, and MS and finally confirmed by single crystal X-ray crystallography.

Photochemical Approach to the Preparation of Lariat Crown Ethers Containing Peptide Sidearms

  • Cho, Dae-Won;Quan, Chunsheng;Park, Hea-Jung;Yoon, Ung-Chan;Mariano, Patrick S.
    • Bulletin of the Korean Chemical Society
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    • v.32 no.2
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    • pp.503-509
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    • 2011
  • New types of lariat type crown ethers containing peptide sidearms were prepared by using a novel strategy employing single electron transfer (SET)-induced photocyclization reactions of $\alpha$-silylether terminated phthalimides. Reactions of chiral substrates in this series produced diastereomeric mixtures of crown ether products as a result of the formation of new stereogenic center generation in the photocyclization process.

First Total Synthesis of (-)-Antofine by Using Catalytic Phase Transfer Alkylation.

  • Lee, Jae-Kwang;Lee, Tae-Ho;Park, Hyeung-Geun;Kim, Deuk-Joon;Kim, Sang-Hee
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.183.3-183.3
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    • 2003
  • Phenanthroindolizidine alkaloid, (-)-antofine has attracted attention because of its extremely potent inhibition of cancer cell growth (Its $IC_50$ values have the low nanomolar range). The frist asymmetric total synthesis of (-)-antofine is described. An important feature of this synthesis is the creation of a stereogenic center by enantioselective alkylation using the phase transfer catalyst (PTC) and ring-closing metathesis (RCM) for pyrrolidine ring construction. This synthesis is efficient to allow the asymmetric preparation of other naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloid.

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Studies Toward the Total Synthesis of Perhydrohistrionicotoxin

  • Ko, Hyo-Jin;Lee, Tae-Ho;Kim, Shin-Ae;Kim, Sang-Hee
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.179.3-179.3
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    • 2003
  • Natural histrionicotoxin, a substance isolated from the skins of the "arrow poison frog" and its fully hydrogenated derivative, perhydrohistrionicotoxin (pHTX), have been the subject of synthetic investigation because of their important neurophysiological activity and a unique framework. In this work, we could obtained the appropriately functionalized spiropiperidine compound as a formal precursor of perhydrohistrionicotoxin. An important feature of this synthesis is the creation of a stereogenic center by using Ireland-Claisen Rearrangement, and Ring-Closing Metathesis (RCM).sis (RCM).

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