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Volumn 38, Issue 46, 1997, Pages 8077-8080

Synthesis of [α-alkyul β-hydroxy diene]iron tricarbonyl complexes of known configuration via trisubstituted epoxides for the synthesis of polyenic macrolactones

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL IRON; IRON COMPLEX; MACROLIDE; POLYENE ANTIBIOTIC AGENT;

EID: 0343145676     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10112-5     Document Type: Article
Times cited : (5)

References (17)
  • 1
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    • Macrolide Antibiotics
    • Ed., Academic Press, Inc.
    • Macrolide Antibiotics, S. Omura Ed., Academic Press, Inc. 1984, Part II: Polyene Macrolides.
    • (1984) Part II: Polyene Macrolides
    • Omura, S.1
  • 2
    • 0011829062 scopus 로고
    • Unfunctionalized dienes : and ref.; functionalized dienes :
    • Unfunctionalized dienes : Graf, R.E.; Lillya, C.P. J. Organomet. Chem. 1979, 166, 53-56 and ref.; functionalized dienes : Franck-Neumann, M.; Sedrati, M.; Mokhi, M. New J. Chem. 1990, 14, 471-480.
    • (1979) J. Organomet. Chem. , vol.166 , pp. 53-56
    • Graf, R.E.1    Lillya, C.P.2
  • 3
    • 0011829062 scopus 로고
    • Unfunctionalized dienes : Graf, R.E.; Lillya, C.P. J. Organomet. Chem. 1979, 166, 53-56 and ref.; functionalized dienes : Franck-Neumann, M.; Sedrati, M.; Mokhi, M. New J. Chem. 1990, 14, 471-480.
    • (1990) New J. Chem. , vol.14 , pp. 471-480
    • Franck-Neumann, M.1    Sedrati, M.2    Mokhi, M.3
  • 7
    • 0031473099 scopus 로고    scopus 로고
    • For a recent review, cf :
    • For a recent review, cf : Donaldson, W.A. Aldrichimica Acta 1997, 30, 17-24.
    • (1997) Aldrichimica Acta , vol.30 , pp. 17-24
    • Donaldson, W.A.1
  • 9
    • 0343629055 scopus 로고    scopus 로고
    • The most suitable substituents for the elaboration of the polyenic framework are probably formyl or hydroxymethyl groups, but these groups can not be present from the beginning (incompatibility with Friedel-Crafts conditions). Subsequent transformation of an ester group is however easy
    • The most suitable substituents for the elaboration of the polyenic framework are probably formyl or hydroxymethyl groups, but these groups can not be present from the beginning (incompatibility with Friedel-Crafts conditions ). Subsequent transformation of an ester group is however easy .
  • 10
    • 33845378961 scopus 로고
    • This reagent is a reducing agent for aldehydes, ketones and acid chlorides but not for esters : The reduction of epoxides was not mentioned, but we observed in the present case that it was much more rapid than the reduction of ketones
    • This reagent is a reducing agent for aldehydes, ketones and acid chlorides but not for esters : Kim, S.; Oh, C.H.; Ko, J.S.; Ahn, K.H.; Kim, Y.J. J. Org. Chem. 1985, 50, 1927-1932. The reduction of epoxides was not mentioned, but we observed in the present case that it was much more rapid than the reduction of ketones .
    • (1985) J. Org. Chem. , vol.50 , pp. 1927-1932
    • Kim, S.1    Oh, C.H.2    Ko, J.S.3    Ahn, K.H.4    Kim, Y.J.5
  • 11
    • 0343193444 scopus 로고    scopus 로고
    • 2, the alcohols 7a2 and 7b (75 %, 1:1) along with minor amounts of the corresponding methyl-epimerized alcohols and ca. 4 % starting material. This allowed the determination of the configuration of 8a/8b4
    • 2, the alcohols 7a2 and 7b (75 %, 1:1) along with minor amounts of the corresponding methyl-epimerized alcohols and ca. 4 % starting material. This allowed the determination of the configuration of 8a/8b.
  • 12
    • 0342758827 scopus 로고
    • Cf. for dimethyl styrene oxides :
    • Cf. for dimethyl styrene oxides : Guyon, R.; Villa, P. Bull. Soc. Chim. Fr. 1975, 2593-2598.
    • (1975) Bull. Soc. Chim. Fr. , pp. 2593-2598
    • Guyon, R.1    Villa, P.2
  • 13
    • 0343629050 scopus 로고    scopus 로고
    • The details of the X-ray structure determinations will be given in the full paper. Ortep views of 7a1, 7a2, 7b (Service Commun de Rayons X de la Federation de Recherche Chimie de l'Université Louis Pasteur)
    • The details of the X-ray structure determinations will be given in the full paper. Ortep views of 7a1, 7a2, 7b (Service Commun de Rayons X de la Federation de Recherche Chimie de l'Université Louis Pasteur) :
  • 15
    • 33749709837 scopus 로고
    • The same substructure (dienic side chain) is found for instance in some cyanobacteria toxins such as nodularin, microcystin or motopurin (cyclic pentapeptides) ;
    • The same substructure (dienic side chain) is found for instance in some cyanobacteria toxins such as nodularin, microcystin or motopurin (cyclic pentapeptides) : Rinehart, K.L.; Harada, K.I.; Namikoshi, M.; Chen, C.; Harris, C.A. J. Amer. Chem. Soc. 1988, 110, 8557-8558 ; De Silva, E.D.; Williams, D.E.; Andersen, R.J.; Klix, H.; Holmes, C.F.B.; Allen, T.M. Tetrahedron Lett. 1992, 33, 1561-1564.
    • (1988) J. Amer. Chem. Soc. , vol.110 , pp. 8557-8558
    • Rinehart, K.L.1    Harada, K.I.2    Namikoshi, M.3    Chen, C.4    Harris, C.A.5
  • 16
    • 0026528205 scopus 로고
    • The same substructure (dienic side chain) is found for instance in some cyanobacteria toxins such as nodularin, microcystin or motopurin (cyclic pentapeptides) : Rinehart, K.L.; Harada, K.I.; Namikoshi, M.; Chen, C.; Harris, C.A. J. Amer. Chem. Soc. 1988, 110, 8557-8558 ; De Silva, E.D.; Williams, D.E.; Andersen, R.J.; Klix, H.; Holmes, C.F.B.; Allen, T.M. Tetrahedron Lett. 1992, 33, 1561-1564.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1561-1564
    • De Silva, E.D.1    Williams, D.E.2    Andersen, R.J.3    Klix, H.4    Holmes, C.F.B.5    Allen, T.M.6
  • 17
    • 0343629048 scopus 로고    scopus 로고
    • 1H-NMR spectra
    • 1H-NMR spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.