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Volumn 47, Issue 22, 2006, Pages 3701-3705

Synthesis of β-chloro α-amino acids: (2S,3R)- and (2S,3S)-3-chloroleucine

Author keywords

Chloro amino acids; Lactones; 3 Chloroleucine; Aeruginosins; Ring opening

Indexed keywords

AMINO ACID DERIVATIVE; BETA CHLOROLEUCINE DERIVATIVE; LACTONE DERIVATIVE; LEUCINE; LITHIUM CHLORIDE; UNCLASSIFIED DRUG;

EID: 33646095237     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.127     Document Type: Article
Times cited : (14)

References (48)
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    • For other natural chloroleucines and their occurrence in Dysidea sponges, see: and references cited therein
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    • We have argued that the structures for aeruginosins 205 should be revised, since when the claimed 6-chlorooctahydroindole ring in the proposed structures was synthesized, its NMR data did not agree with those reported for the azabicyclic amino acid of the aforementioned natural products. For the synthesis of the putative core of aeruginosins 205, see:
    • We have argued that the structures for aeruginosins 205 should be revised, since when the claimed 6-chlorooctahydroindole ring in the proposed structures was synthesized, its NMR data did not agree with those reported for the azabicyclic amino acid of the aforementioned natural products. For the synthesis of the putative core of aeruginosins 205, see:. Valls N., Vallribera M., Font-Bardía M., Solans X., and Bonjoch J. Tetrahedron: Asymmetry 14 (2003) 1241-1244
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    • For the reactivity of β-lactones derived from l-threonine and related amino acids, see:
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    • note
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    • For a review on the synthesis of optically active β-lactones, see:
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    • For the synthesis of β-substituted N-protected α-amino-β-lactones promoted by treatment of N-(o-nitrophenyl)sulfenyl derivatives of β-hydroxy α-amino acids with 4-bromobenzenesulfonyl chloride, see:. Pu Y., Martin F.M., and Vederas J.C. J. Org. Chem. 56 (1991) 1280-1283
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    • note
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    • note
    • 2O, see Ref. 9a.
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    • note
    • 2), 84.6 (C4), 128.5, 128.7, 128.8, 135.8 (Ar), 155.6 (CO), 168.8 (C2). All new compounds were characterized by HRMS or microanalysis.
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    • 33646116501 scopus 로고    scopus 로고
    • note
    • 2), 128.0, 128.3, 128.5, 135.7 (Ar), 156.8 (NCO), 173.6 (C1).
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    • For the synthesis of (2R,3S)- and (2S,3R)-2-amino-3-chlorobutanoic acid (β-chlorothreonines) by optical resolution of the racemic form, see:
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    • To our knowledge there is only one precedent of β-lactonization of 3-hydroxyleucine derivatives in the literature, involving the (2S,3S)-N,N-dibenzyl derivative:
    • To our knowledge there is only one precedent of β-lactonization of 3-hydroxyleucine derivatives in the literature, involving the (2S,3S)-N,N-dibenzyl derivative:. Laib T., Chastanet J., and Zhu J. J. Am. Chem. Soc. 124 (2002) 583-590
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    • note
    • 2O); NMR data, see Table 1.
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    • For the enantioselective synthesis of the four stereoisomeric 3-hydroxyleucines, see:
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    • note
    • 2), 128.4, 128.7, 128.9, 136.2 (Ar), 156.9 (NCO), 175.2 (C-1). Compound 2, see Table 1. LC-MS of the product indicated that a small amount of an N-ethyl derivative had formed.
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    • For the synthesis of (2S,3S)-(+)-3-fluoroleucine, see:
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.