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Volumn 11, Issue 20, 2009, Pages 4664-4667

Efficient total synthesis of (-)-kaitocephalin

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCINE; KAITOCEPHALIN; PYRROLE DERIVATIVE;

EID: 70349932310     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9019343     Document Type: Article
Times cited : (31)

References (42)
  • 2
    • 0027686249 scopus 로고
    • (b) Coyle, J. T.; Puttfarcken, P. Science 1993, 262, 689-695.
    • (1993) , vol.262 , pp. 689-695
    • Coyle, J.T.1    Science, P.P.2
  • 7
    • 0034059343 scopus 로고    scopus 로고
    • (c) Lees, G. J. Drugs 2000, 59, 33-78.
    • (2000) J. Drugs , vol.59 , pp. 33-78
    • Lees, G.1
  • 15
    • 70349898145 scopus 로고    scopus 로고
    • 6
    • 6
  • 16
    • 0035802368 scopus 로고    scopus 로고
    • Synthesis of 2-epimer of 1
    • Synthesis of 2-epimer of 1: Ma, D.; Yang, J. J. Am. Chem. Soc. 2001, 123. 9706-9707.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9706-9707
    • Ma, D.1    Yang, J.2
  • 25
    • 70349904334 scopus 로고    scopus 로고
    • For procedures for the conversion of 8a to 9a and 13 to 9b and the NOE correlation of 9a and X-ray structure of 9b, see Supporting Information.
    • For procedures for the conversion of 8a to 9a and 13 to 9b and the NOE correlation of 9a and X-ray structure of 9b, see Supporting Information.
  • 26
    • 70349932223 scopus 로고    scopus 로고
    • 1H NMR spectrum of the crude 8b, but the exact ratio could not be determined because of their broard signals. The contaminated diastereomers were chromatographically removed during its conversion to 11.
    • 1H NMR spectrum of the crude 8b, but the exact ratio could not be determined because of their broard signals. The contaminated diastereomers were chromatographically removed during its conversion to 11.
  • 27
    • 70349915819 scopus 로고    scopus 로고
    • 2-DMSO, or 1-Me-AZADO.
    • 2-DMSO, or 1-Me-AZADO.
  • 29
    • 70349911638 scopus 로고    scopus 로고
    • The yield was calculated after conversion to 13 since the OBO ester 11 was labile upon chromatographic isolation or storage under ambient conditions for gradual conversion to the partially hydrolyzed 12. Contrary to 11, its C3-epimers 8a,b are quite stable under these conditions.
    • The yield was calculated after conversion to 13 since the OBO ester 11 was labile upon chromatographic isolation or storage under ambient conditions for gradual conversion to the partially hydrolyzed 12. Contrary to 11, its C3-epimers 8a,b are quite stable under these conditions.
  • 30
    • 70349931232 scopus 로고    scopus 로고
    • 4 is under investigation and will be reported in due course.
    • 4 is under investigation and will be reported in due course.
  • 31
    • 70349915817 scopus 로고    scopus 로고
    • CCDC 738627 (9b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via deposit.
    • CCDC 738627 (9b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via http://www.ccdc.cam.ac.uk/ deposit.
  • 32
    • 0002325951 scopus 로고
    • Synthesis of (Z)-α.β-dehydroamino acid ester by HWE reaction
    • Synthesis of (Z)-α.β-dehydroamino acid ester by HWE reaction: Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-60.
    • (1984) Synthesis , pp. 53-60
    • Schmidt, U.1    Lieberknecht, A.2    Wild, J.3
  • 34
    • 70349915820 scopus 로고    scopus 로고
    • The chemical shift of the amide proton in (E)-2 appeared at
    • The chemical shift of the amide proton in (E)-2 appeared at δ 8.1.
    • δ 8.1.
  • 35
    • 0033618118 scopus 로고    scopus 로고
    • For representative examples of the synthesis of α.β- dehydroalanine derivatives, see: (a)
    • For representative examples of the synthesis of α.β- dehydroalanine derivatives, see: (a) Stohlmeyer, M. M.; Tanaka, H.; Wandless, T. J. J. Am. Chem. Soc. 1999, 121, 6100-6101.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 6100-6101
    • Stohlmeyer, M.M.1    Tanaka, H.2    Wandless, T.J.3
  • 39
  • 41
    • 70349897246 scopus 로고    scopus 로고
    • Asymmetric hydrogenation of (E)-2 using (R,R)-QuinoxP* did not react at all resulting in the complete recovery of (E)-2, whereas (S,S) -QuinoxP* gave a mixture of 14a and 14b in 71% yield (14a/14b = 26:74).
    • Asymmetric hydrogenation of (E)-2 using (R,R)-QuinoxP* did not react at all resulting in the complete recovery of (E)-2, whereas (S,S) -QuinoxP* gave a mixture of 14a and 14b in 71% yield (14a/14b = 26:74).
  • 42
    • 70349913799 scopus 로고    scopus 로고
    • Note
    • 1H NMR. However, the HPLC separation of each isomer was accompanied by a significant loss of the product (see Supporting Informationand ref 5). An improved method for their separation is currently being investigated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.