• 제목/요약/키워드: lactonization

검색결과 14건 처리시간 0.034초

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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    • 제15권10호
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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.

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

  • 서영거;구본암;정재경;조윤상;나운용
    • 약학회지
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    • 제37권3호
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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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Carpenter bee pheromone의 2-methyl-5(S)-hexanolide의 부분 입체선택적 합성 (The diastereoselective synthesis of 2-methyl-5(S)-hexanolide)

  • 장재혁;이상준;김정한
    • Applied Biological Chemistry
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    • 제37권1호
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    • pp.25-29
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    • 1994
  • Ethyl acetoacetate를 빵효모가 환원해 생산한 ethyl-(S)-3-hydroxy-butyrate(2a)를 키 랄 출발물질로 하여 수목에 피해를 끼치는 해충인 carpenter bee의 수컷이 분비하는 성 페로몬인 cis-2-methyl-5-hexanolide(1)을 diastereomer로 합성하였다. 역합성적 분석을 통한 합성계획으로부터 T-Goal로 Wittig반응을 잡고 출발물질을 환원하여 얻은 알데히드 4와 triethyl 2-phosphonopropionate(7)을 Horner-Emmons반응시켜 ${\alpha},{\beta}$-불포화 에스테르 5를 얻은 뒤 catalytic hydrogenation과 lactonization을 시켜 carpenter bee 페로몬 1을 전체수율 37%로 쉽고 간단하게 합성하였다.

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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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    • 제30권5호
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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.