• Title/Summary/Keyword: Regioselective synthesis

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Direct Organocatalytic Regioselective α-Hydroxyamination of α-Branched Aldehydes

  • Kim, Sung-Gon;Ahn, Eun-Ju;Park, Tae-Ho
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1665-1669
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    • 2007

  • A direct regioselective α-hydroxyamination of α-branched aldehydes with nitrosobenzene using cis-5-benzylproline as catalyst has been developed for the preparation of α-hydroxyamino aldehydes possessing a quaternary carbon center. Such compounds are versatile building blocks for the synthesis of quaternary α- amino acids, β-amino alcohols, and 1,2-diamines.

  • https://doi.org/10.5012/bkcs.2007.28.10.1665 인용 PDF KSCI

Regioselective synthesis of .alpha.-L-fucosyl-containing benzyl disaccharides by use of .alpha.-L-fucosidases of aspergillus niger

  • Chung, Yong-Za;Kwak, Hong-Keun;Sung, Yung-Ki
    • Archives of Pharmacal Research
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    • v.19 no.4
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    • pp.307-311
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    • 1996

  • The activity of fucosidase shows different value depending on disease, eg) fucosidosis and I cell disease are characterized by the absence or deficiences of .alpha.-fucosidase, and sera of ovarian cancer patients exhibited a statistically significant deficiency of .alpha.-L-fucosidase activity (Zielke et al., 1972; Kress et al., 1980; Barlow et al., 1981). For the purpose of diagnosis of these disease easily, the manual of test can be developed by preparing kits of hydrophobic-binding substrate of fucosidase that bind C18-column.

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Design and Synthesis of (${\pm}$) -3-Deoxygericudranin A as an Antitumour Agent (항암제로서의 (${\pm}$) -3-데옥시제리쿠드라닌 A의 설계 및 합성)

  • Choi, Yoon-Jung;Shim, Pil-Jong;Kim, Hee-Doo
    • YAKHAK HOEJI
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    • v.41 no.1
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    • pp.14-17
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    • 1997

  • (${\pm}$)-3-Deoxygericudranin A was designed and synthesized for the development of novel antitumour agent and for the elucidation of the effect of 3-hydroxyl group in gericudranin A on antitumour activity. 2,4.6-Trihydroxyacetophenone was converted to 3-deoxygericudranin A in 5 steps via sequential protection, aldol condensation, Michael tvpe-cyclization, regioselective, C-benzylation and deprotection.

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An efficient Procedure for the Regioselective Synthesis of 10-Methoxy-11-Hydroxyaporphine from (R,S)-10,11-Dihydroxyaporphine

  • Kim, Jack C.
    • Archives of Pharmacal Research
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    • v.17 no.3
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    • pp.204-206
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    • 1994

  • A regioselective perparation of 10-methoxy-11-hydroxyaporphine ("Apocodeine, 1b") form (R, S)-10, 11-dihydroxyaporphine(apomorphine, 1a) is described. The isopropylidene ketal ring of 10, 11-(isopropylidenyldioxy) aporphine (2) obtained by the isopropylidenation of apomorphine, was regioselectively opened by the ten equivalent of timethylaluminum to give 100-hydroxy-11-t-butyloxyaporphine (3). The free 10-hydroxyl position of 3 was methylated with methyl p-toluenesulfonate/NaH, and afforded 10-methoxy-11-t-butyloxyaporphine (4) in high yield. Selective debutylation gave the desired 10-methoxy-11-hydroxyaporphine("apocodeine", 1b) in good yield.

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Formal Synthesis of Sex Pheromone of Gypsy Moth (+)-Disparlure from L-(+)-Tartaric Acid

  • Gi Baek Gwon;Hang Soo Kim;Jae Won Park;Jong Soo Choi;Kyung Oh Doh;Kyung Jin Kim;Young Bae, Seu
    • Journal of the Korean Chemical Society
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    • v.68 no.3
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    • pp.131-134
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    • 2024

  • A simple strategy for the formal synthesis of the sex pheromone of gypsy moth (+)-disparlure from L-(+)-tartaric acid is described herein. The key steps include the mono-esterification and regioselective ring-opening of an epoxide using a Grignard reagent. The strategy of conferring asymmetry using 2-butanone enables mono-esterification in high yield and reduces the number of steps. Subsequently, (+)-disparlure is synthesized via the regioselective ring opening of the epoxide.

  • https://doi.org/10.5012/jkcs.2024.68.3.131 인용 PDF HTML