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서영란,김영규,채다원,김현정 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.1
The development of an efficient synthetic method for threo-vicinal amino hydroxy acids had been an attractive subject since non-proteinogenic amino acids had been frequently found in biologically active natural products. In this presentation, a newly synthesized synthon, trans-5-methoxycarbonyl-oxazolidine, was obtained with more than 20 to 1 stereoselectivity via the cascade reactions between N-hydroxymethyl protected α-amino aldehyde and PhSO<sub>2</sub>CH<sub>2</sub>NO<sub>2</sub>, and the following in-situ ozonolysis. Five precursors for threo-β-amino-α-hydroxy acids was synthesized in 65~72% yields from the stable α-amino aldehydes.
Efficient synthesis of natural aminopeptidase inhibitors, bestatin and AHPBA-Val
서영란,김영규,채다원 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.1
Bestatin and AHPBA-Val are known as inhibitors to aminopeptidase N (APN). The bioactivity of bestatin and AHPBA-Val is closely related to the stereochemistry of β-amino-α-hydroxy acid moiety. However, the desired stereochemistry had been mostly given by chiral catalysts or chiral auxiliaries. Contrast to the previous reagent controlled methods, the chiral synthon for (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid was stereoselectively prepared from the N-hydroxymethyl protected α-amino aldehyde via the intramolecular conjugate addition. The prepared synthon, trans-methoxymethyl-oxazolidine, was converted to bestatin and AHPBA-Val in 85% and 62% yields via 4 steps without separate production and deprotection steps of the vicinal amino alcohol.
Eun-Sil Kang,채다원,Baekjin Kim,김영규 한국공업화학회 2012 Journal of Industrial and Engineering Chemistry Vol.18 No.1
2,5-Dihydroxymethylfuran (DHMF) and 5-hydroxymethylfuranoic acid (HMFA) are the versatile intermediate chemicals of high industrial potential. An efficient preparation of both DHMF and HMFA is reported from biomass-derived HMF via a Cannizzaro reaction using ionic liquids as a reusable reaction solvent under the water-free conditions. The operationally simple and environment-friendly process produces both DHMF and HMFA from HMF consistently in good to high yields up to five runs with the recycled ionic liquid.