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The Practical Asymmetric Syntheses of Key chiral Intermediates of chiral Drug from Four-Carbon chiral pool

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Chemical Research in Chinese Universities 2001年第Z1期17卷 134-135页

作者： MI AiQiao Chengdu Institute of Organic Chemistry Chinese Academy of Sciences

(S)-or (R)-2-Amino-4-phenylbutyric acid and (S)-or (R)-2-hydroxy-4-phenylbutyric acid and their ethyl esters are key chiral intermediates for the preparation of angiotensin converting enzyme inhibitors (ACEI) and other chiral drugs. Their practically asymmetric synthetic methods in large scale from four-carbon chiral pool, commercially available L-aspartic acid and L-malic acid, will be presented (as scheme).(S)-2-Amino-4-phenylbutyric acid and its ethyl ester hydrochloride were prepared from the easily available L-aspartic acid via activation by forming anhydride hydrochloride, Friedel-Crafts reaction with benzene, hydrogenolysis and esterification with ethanol in the presence of thionyl chloride in overall yield of 80% and 73.6% respectively with 99% ee. We first used amino acid anhydride hydrochloride as the acylating agent in Friedel-Crafts reaction without racemization. [1]

关键词： angiotensin converting enzyme inhibitors thionyl chloride chiral pool amino acid

Syntheses of(R)-and(S)-3-Methylheptanoic Acids

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中国化学:英文版 2015年第6期33卷 674-678页

作者： Shunji Zhang Yong Shi Weisheng Tian CAS Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

Starting from chiral methyl molecules 3 and 4,both derived from(R)-4-methyl-δ-valerolactone,we have ac-complished the synthesis of(R)and(S)-3-methylheptanoic *** methods are amendable to the syntheses of a wide varie... 详细信息

关键词： pheromones chiral pool natural products total synthesis (R)-4-methyl-δ-valerolactone

Synthesis of C1-C9 Domain of the Nominal Didemnaketal A

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中国化学:英文版 2015年第6期33卷 663-668页

作者： Shunji Zhang Yong Shi Weisheng Tian CAS Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

Based on chiral pool strategy,a synthesis of the C1-C9 domain of the proposed structure of didemnaketal A,a natural product with potent HIV-1 protease inhibitory activity,has been *** transformations are a Shar-pless ... 详细信息

关键词： didemnaketal chiral pool chelation-controlled allylation natural products Sharpless AD

Synthesis of(R)-(−)-Muscone from(R)-5-Bromo-4-methylpentanoate:A Chiron Approach

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中国化学:英文版 2015年第6期33卷 683-687页

作者： Junwei Shen Yong Shi Weisheng Tian CAS Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

A synthesis of(R)-muscone(1),a valuable musk odorant,is *** stereogenic center of muscone was introduced from methyl(R)-5-bromo-4-methylpentanoate(5),a chiral pool molecule developed in our group,and the macrocyclic r... 详细信息

关键词： muscone fragrances macrocycles chiral pool (R)-5-bromo-4-methylpentanoate