- Synthesis of (3S,4S)-statine and a related compound, (3S,4S)-AHPPA, from D-glucosamine as a chiral pool
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Biologically important threo-β-hydroxy-γ-amino acids, (3S,4S)-statine ((3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid) (1) and (3S,4S)-AHPPA (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid) (2), were synthesized starting from D-glucosamine (3) as a chiral pool. Two routes for the transformation of D-glucosamine to key intermediates, which are applicable to the synthesis of threo-β-hydroxy-γ-amino acids, were investigated. The successful route involved C(6)-carbon degradation and elimination of the C(4)-hydroxy group of D-glucosamine in 8 steps and 30% overall yield to furnish (4R,5S)-2-oxo-5-vinyloxazolidine-4-carbaldehyde dimethyl acetal (17), which has been utilized as a versatile intermediate for synthesizing the target compounds.
- Shinozaki, Katsuo,Mizuno, Kazuhiro,Oda, Hirohisa,Masaki, Yukio
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p. 1737 - 1745
(2007/10/03)
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- Enantiospecific Synthesis of (3S,4S)-Statine and Its Analogue from D-Glucosamine as a Chiral Pool
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The C(6)-carbon degradation and elimination C(4)-hydroxy group of D-glucosamine were achieved in 8-steps and 30percent overall yield to furnish (4R,5S)-5-vinyl-2-oxazolidinone-4-carbaldehyde dimethyl acetal, which was utilized as a key intermediate for en
- Shinozaki, Katsuo,Mizuno, Kazuhiro,Oda, Hirohisa,Masaki, Yukio
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p. 2265 - 2268
(2007/10/02)
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- Syntheses and reactions of silyl carbamates. 2. A new mode of cyclic carbamate formation from tert-butyldimethylsilyl carbamate
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Stereoselective construction of 1,2 and 1,3 amino hydroxyl systems was achieved by the intramolecular trapping of the N-tert-butyldimethylsilyloxycarbonyl species (silyl carbamate) activated by fluoride ion. The reaction of the silyl carbamate with 1,2-sy
- Sakaitani, Masahiro,Ohfune, Yasufumi
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p. 1150 - 1158
(2007/10/02)
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- A NEW MODE OF CYCLIC CARBAMATE FORMATION VIA tert.-BUTYLDIMETHYLSILYL CARBAMATE. STEREOSELECTIVE SYNTHESES OF STATINE AND ITS ANALOGUE
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Stereoselective construction of 1,2- and 1,3-amino hydroxyl systems was carried out using SN2' (initiated by AgF or AgF-Pd(II)) cyclic carbamate formations from tert.-butyldimethyl silyl carbamates.This method was applied to the syntheses of st
- Sakaitani, Masahiro,Ohfune, Yasufumi
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p. 3987 - 3990
(2007/10/02)
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