메뉴 건너뛰기




Volumn 15, Issue 7, 2004, Pages 1181-1186

Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-δ- hydroxyisoleucine, noncoded amino acid of halipeptin A

Author keywords

[No Author keywords available]

Indexed keywords

(TERT BUTYLDIMETHYLSILYL) 2 BUTYN 1 OL; AMINO ACID DERIVATIVE; HALIPEPTIN A; LEUCINE; METHYL GROUP; N METHYL DELTA HYDROXYISOLEUCINE; NITROGEN; OXAZOLIDINONE DERIVATIVE; OXYGEN; SILANE; TRIETHYLSILANE; UNCLASSIFIED DRUG;

EID: 1642587817     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.02.008     Document Type: Article
Times cited : (33)

References (23)
  • 1
    • 0041475925 scopus 로고    scopus 로고
    • and references cited therein
    • Davies J.S. J. Peptide Sci. 9:2003;471-501. and references cited therein.
    • (2003) J. Peptide Sci. , vol.9 , pp. 471-501
    • Davies, J.S.1
  • 3
    • 0035823849 scopus 로고    scopus 로고
    • Halipeptins also show a promising antitumor activity, being cytotoxic against HCT-116 human colon carcinoma cells in nanomolar range. William Fenical, personal communication
    • Randazzo A., Bifulco G., Giannini C., Bucci M., Debitus C., Cirino G., Gomez-Paloma L. J. Am. Chem. Soc. 123:2001;10870-10876. Halipeptins also show a promising antitumor activity, being cytotoxic against HCT-116 human colon carcinoma cells in nanomolar range. William Fenical, personal communication.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10870-10876
    • Randazzo, A.1    Bifulco, G.2    Giannini, C.3    Bucci, M.4    Debitus, C.5    Cirino, G.6    Gomez-Paloma, L.7
  • 5
    • 0342436140 scopus 로고
    • A synthesis of a mixture of diastereoisomes of δ-hydroxyisoleucine has been previously reported by
    • A synthesis of a mixture of diastereoisomes of δ-hydroxyisoleucine has been previously reported by Englisch-Peters S. Tetrahedron. 45:1989;6127-6134.
    • (1989) Tetrahedron , vol.45 , pp. 6127-6134
    • Englisch-Peters, S.1
  • 19
    • 1642585285 scopus 로고    scopus 로고
    • note
    • 13C NMR) for compounds containing the 5-oxazolidinone ring 13-15 was possible at 80 °C or higher temperatures (see Experimental section).
  • 20
    • 1642601023 scopus 로고    scopus 로고
    • note
    • No substantial improvement of the yields were noted when different reaction conditions were used: 9-BBN as hydroborating agent, excess of reagents (4.0-6.0 equiv), different reaction times (3-12 h) and temperatures of reaction ( - 10 °C to rt).
  • 23
    • 1642632037 scopus 로고    scopus 로고
    • note
    • To overcome the problem of the low yielding benzyl protection and reductive oxazolidinone opening, we subjected compound 14 to a direct reductive oxazolidinone ring opening. Unfortunately, from the complex crude reaction mixture, only compound 16 ((3S,4S)-3-[(9H-fluoren-9-ylmethoxycarbonyl)- methylamino]-4-methyl-tetrahydro-2H-pyran-2-one) could be isolated in 30% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.