• Title/Summary/Keyword: Stereoselective synthesis

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Synthesis of Carbocycles Using Metal Catalyst(I) -Stereoselective Synthesis of Cyclopentane Using Pd(0) Catalyst- (금속 촉매를 이용한 Carbocycle의 합성(I) -Pd(0) 촉매를 이용한 Cyclopentane의 입체선택적 합성-)

  • Suh, Young-Ger;Lee, Gi-Ho;Cho, Youn-Sang
    • YAKHAK HOEJI
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    • v.34 no.5
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    • pp.287-290
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    • 1990
  • An efficient stereoselective synthetic route to carbocycle is described. 1,1,2-Trisubstituted cyclopentane was synthesized from allylic carbonate by Pd(0) catalyzed cyclization.

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Stereoselective Transformation of Phytosphingosine to Safingol

  • Kim, Na-Ri;Lee, Sun-Hee;Namgoong, Sung-Keon
    • Bulletin of the Korean Chemical Society
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    • v.30 no.3
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    • pp.695-699
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    • 2009
  • A short and efficient synthesis of (2S,3S)-safingol from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The highlights of the synthesis are a stereoselective one-pot transformation of a diol into an epoxide under phase transfer catalytic conditions and a regioselective epoxide-opening reduction with a hydride reagent.

Synthesis of an Intermediate for Carbaprostacyclin: Stereoselective Synthesis of 1-Alkoxy-3-benzenesulfonyl-3-cyano-4-ethenyl cyclopentane (카바프로스타싸이클린 중간체의 합성 : 1-Alkoxy-3-benzenesulfonyl-3-cyano-4-ethenyl cyclopentane의 입체선택적 합성)

  • 서영거;정재경;구본암;최영기;조윤상
    • YAKHAK HOEJI
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    • v.39 no.1
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    • pp.41-47
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    • 1995
  • An efficient and stereoselective synthetic route to the trisubstituted hydroxy cyclopentane as an useful synthetic intermediate for carbaprostacyclin is described. Pd(0)-mediated intramolecular alkylation of allylic carbonate has been employed as a key reaction.

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Stereoselective Synthesis of a Novel Cyclohexene Version of Carbovir

  • Li, Hua;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1645-1650
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    • 2007
  • This paper describes a racemic and stereoselective synthetic route for a novel cyclohexenyl carbocyclic adenine analogue. The required stereochemistry of the target compound was controlled using a stereoselective glycolate Claisen rearrangement followed by α-chelated carbonyl addition. The introduction of 6-chloropurine was achieved using Mitsunobu conditions, and further modifications of the corresponding heterocycle gave the target cyclohexenyl nucleoside.

Stereoselective Synthesis of L-Deoxyaltronojirimycin from L-Serine

  • Rengasamy, Rajesh;Curtis-Long, Marcus J.;Ryu, Hyung-Won;Oh, Kyeong-Yeol;Park, Ki-Hun
    • Bulletin of the Korean Chemical Society
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    • v.30 no.7
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    • pp.1531-1534
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    • 2009
  • (2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.