• Title/Summary/Keyword: Epoxide opening

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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

Regiospecific Ring-Opening of Unsymmetrical Epoxides to the Corresponding Less Substituted Alcohols by Newly-Devised Meerwein-Ponndorf-Verley Type Reagents

  • Cha, Jin Soon
    • Journal of Integrative Natural Science
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    • v.5 no.2
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    • pp.91-99
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    • 2012

  • A newly-devised Meerwein-Ponndorf-Verley (MPV) reagents, such as diisobutylacetoxyalanes and diisobutylmethanesulfonylalanes, achieved a clean conversion of unsymmetrical epoxides to the corresponding less substituted alcohols. This review covers the recent developments for such a regiospecific ring-opening reaction of epoxides.

  • https://doi.org/10.13160/ricns.2012.5.2.091 인용 PDF

From L-Ascorbic Acid to Protease Inhibitors: Practical Synthesis of Key Chiral Epoxide Intermediates for Aspartyl Proteases

  • Chang, Sun-Ki;So, Soon-Mog;Lee, Sang-Min;Kim, Min-Kyu;Seol, Kyoung-Mee;Kim, Sung-Min;Kang, Jae-Sung;Choo, Dong-Joon;Lee, Jae-Yeol;Kim, B.-Moon
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2213-2218
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    • 2012

  • Efficient synthetic routes were developed to prepare a sizable amount (4-15 grams) of the chiral epoxides 4-6 as versatile intermediates for the synthesis of aspartyl protease inhibitors of therapeutic interest such as HIV protease and ${\beta}$-secretase. Oxidative cleavage of the C(2)-C(3) double bond of L-ascorbic acid followed by functional group manipulation led to the preparation of the epoxide 10, which was opened with an azide to yield a common aziridine intermediate 12. Through opening of the aziridine ring of 12 with either a carbon or a sulfur nucleophile, chiral epoxide precursors 4-6 could be prepared for various HIV protease inhibitors. Except for the final low melting epoxides 5 and 6, all intermediates were obtained as crystalline solids, thus the synthetic pathway can be easily applied to a large-scale synthesis of the chiral epoxides.

  • https://doi.org/10.5012/bkcs.2012.33.7.2213 인용 PDF KSCI