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Volumn , Issue 17, 2005, Pages 2615-2618

Total synthesis of sperabillin A and C

Author keywords

Antibiotics; Henry reaction; Pseudo peptides; Ruthenium tetroxide; Sperabillins

Indexed keywords

3 AMINOPROPIONAMIDINE; 3,6 DIAMINO 5 HYDROXYHEXANOIC ACID; ALDEHYDE; AMIDINE; ANTIBIOTIC AGENT; BENZENE; DIAMINO ACID; HEXANOIC ACID DERIVATIVE; N TERT BUTYLOXYCARBONYL TYROSINE; NEGAMYCIN; RUTHENIUM DERIVATIVE; SPERABILLIN A; SPERABILLIN C; TYROSINE; UNCLASSIFIED DRUG;

EID: 27444441454     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917106     Document Type: Article
Times cited : (16)

References (39)
  • 2
    • 27444446122 scopus 로고    scopus 로고
    • Eur. Pat. Appl.; EP206068, 1986
    • (a) Harada, S.; Ono, H. Eur. Pat. Appl.; EP206068, 1986.
    • Harada, S.1    Ono, H.2
  • 18
    • 27444440580 scopus 로고    scopus 로고
    • note
    • The reaction of chiral aldehyde 6 with nitromethane in the presence of catalyst (+)-11 represents the matched case of double diastereoselection, since application of the enantiomeric catalyst (-)-11 gave the corresponding epimer of 5 with slightly lower stereoselectivity (91% de).
  • 24
    • 0037450411 scopus 로고    scopus 로고
    • (f) For a recent review covering the oxidative degradation of benzene rings see: Mander, L. N.; Williams, C. M. Tetrahedron 2003, 59, 1105.
    • (2003) Tetrahedron , vol.59 , pp. 1105
    • Mander, L.N.1    Williams, C.M.2
  • 27
    • 27444440324 scopus 로고    scopus 로고
    • note
    • 2O = 2:2:3, r.t.] previously developed by Sharpless and co-workers (see ref. 13b) gave the oxidation product 10 in a 41% yield together with 24% of the N-formyl derivative mentioned above.
  • 29
    • 27444445115 scopus 로고    scopus 로고
    • note
    • In the absence of sodium hydrogen carbonate a somewhat lower yield (56%) of product 10 was obtained.
  • 30
    • 27444435307 scopus 로고    scopus 로고
    • note
    • 4): δ = -5.0, 18.4, 25.9, 28.3, 40.0, 43.5, 45.2, 45.8, 67.7, 79.6, 157.1, 178.6.
  • 32
    • 27444432922 scopus 로고    scopus 로고
    • note
    • For an alternative stereoselective approach to (2E,4Z)-hexa-2,4-dienoic acid (14), see ref. 5b.
  • 36
    • 9344243519 scopus 로고
    • For a previous synthesis of 3-aminopropionamidine, starting from 3-aminopropionitril, see: Hilgetag, G.; Paul, H.; Günther, J.; Witt, M. Chem. Ber. 1964, 97, 704.
    • (1964) Chem. Ber. , vol.97 , pp. 704
    • Hilgetag, G.1    Paul, H.2    Günther, J.3    Witt, M.4
  • 38
    • 27444442510 scopus 로고    scopus 로고
    • note
    • 2O): δ = 16.0, 35.3, 38.0, 39.2, 39.8, 47.8, 49.1, 69.1, 125.1, 129.6, 139.4, 139.5, 171.7, 172.4, 174.7.
  • 39
    • 27444445891 scopus 로고    scopus 로고
    • note
    • 2O): δ = 20.7, 35.3, 38.0, 39.2, 39.8, 47.8, 49.1, 69.1, 122.9, 132.0, 143.2, 145.4, 171.6, 172.5, 174.7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.