• Title/Summary/Keyword: Lactonization

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Stereoselective Halolactonization of$\alpha-Phenylsulfonyl-\gamma,\delta$-Unsaturated Amides

  • Lee, Jae-Wook;Jung, Jin-Hang;Oh, Dong-Young
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.842-845
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    • 1994
  • Iodine-induced lactonization of ${\alpha}$-Phenylsulfonyl-${\gamma},{\delta}$-Unsaturated Amides provided 2,4-trans-substitued ${\gamma}$-butyrolactones in high selectivity. NBS-or NCS-induced lactonization of N,N-dimethyl-2-(phenylsulfonyl)-4-pentenamide in DME-$H-2O(2:1 vol)$ gave 2-halo-4-(halomethyl)-2-(phenylsulfonyl)-${\gamma}$-butyrolactone.

Synthesis of Hydroxycyclopentane as a Synthetic Intermediate for Carbaprostacyclin (카바프로스타싸이클린의 중간체로 이용가능한 히드록시싸이클로펜탄의 합성)

  • 서영거;구본암;정재경;조윤상;나운용
    • YAKHAK HOEJI
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    • v.37 no.3
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    • pp.290-294
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    • 1993
  • An efficient synthetic route to the trisubstituted cyclopentane as an useful synthetic intrermediate for carbaprostacyclin is described. Ireland Claisen rearrangement of a hydroxylactone has been employed as a key reaction.

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The diastereoselective synthesis of 2-methyl-5(S)-hexanolide (Carpenter bee pheromone의 2-methyl-5(S)-hexanolide의 부분 입체선택적 합성)

  • Chang, Jay-Hyok;Lee, Sang-Jun;Kim, Jung-Han
    • Applied Biological Chemistry
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    • v.37 no.1
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    • pp.25-29
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    • 1994
  • 2-methyl-5(S)-hexanolide(1); the major component of pheromonal blend of the male carpenter bee was synthesized via Homer-Emmons reaction from Ethyl(S)-3-hydroxybutyrate(2a) which had been obtained by Baker's Yeast reduction in overall yield 39%.

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Expedient One-Pot Synthesis of γ-hydroxybutenolides Starting from Baylis-Hillman Adducts: Lactonization, Isomerization, and Aerobic Oxidation of α-Methylene-γ-hydroxyester

  • Kim, Ko-Hoon;Lee, Hyun-Seung;Kim, Sung-Hwan;Lee, Ka-Young;Lee, Ji-Eun;Kim, Jae-Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.30 no.5
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    • pp.1012-1020
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    • 2009
  • We developed an efficient three-step synthetic protocol of $\gamma$-hydroxybutenolides starting from the Baylis-Hillman adducts: (i) bromination, (ii) Barbier reaction and (iii) one-pot $K_2CO_3$-mediated synthesis of $\gamma$-hydroxybutenolides. In addition, we showed the synthetic applicability of butenolides including self-dimerization, conjugate addition reaction, and alkylations.