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Volumn 4, Issue 7, 2002, Pages 1111-1113

Nucleophilic Addition Reaction of 2-Trimethylsilyloxyfuran to N-Gulosyl-C-alkoxymethylnitrones: Synthetic Approach to Polyoxin C

Author keywords

[No Author keywords available]

Indexed keywords

2 TRIMETHYLSILYLOXYFURAN; 2-TRIMETHYLSILYLOXYFURAN; ANTIFUNGAL AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; POLYOXIN C;

EID: 0037018484     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0200044     Document Type: Article
Times cited : (31)

References (38)
  • 4
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    • and references therein
    • (c) Hahn, H.; Heitsch, H.; Rathmann, R.; Zimmermann, G.; Bormann, C.; Zähner, H.; König, W. A. Liebigs Ann. Chem. 1987, 803-807 and references therein. Krainer, E.; Becker, J. M.; Naider, F. J. Med. Chem. 1991, 34, 174-180 and references therein.
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  • 22
    • 0003416748 scopus 로고
    • Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: New York
    • For reviews for synthesis of optically active α-amino acids, see: (a) Williams, R. M. Synthesis of Optically Active α-Amino Acids: Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: New York, 1989.
    • (1989) Synthesis of Optically Active α-Amino Acids
    • Williams, R.M.1
  • 24
    • 0038106171 scopus 로고    scopus 로고
    • For an excellent review for addition of organometallic reagents to C=N bonds, see: Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 25
    • 0034043296 scopus 로고    scopus 로고
    • For a review for nucleophilic additions to nitrones, see: Lombardo, M.; Trombini, C. Synthesis 2000, 759-774. See also: Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326.
    • (2000) Synthesis , pp. 759-774
    • Lombardo, M.1    Trombini, C.2
  • 26
    • 0034614462 scopus 로고    scopus 로고
    • For a review for nucleophilic additions to nitrones, see: Lombardo, M.; Trombini, C. Synthesis 2000, 759-774. See also: Lombardo, M.; Trombini, C. Tetrahedron 2000, 56, 323-326.
    • (2000) Tetrahedron , vol.56 , pp. 323-326
    • Lombardo, M.1    Trombini, C.2
  • 27
    • 0029034764 scopus 로고
    • For reviews for nucleophilic additions of 2-siloxyfurans, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
    • (1995) Synthesis , pp. 607-626
    • Casiraghi, G.1    Rassu, G.2
  • 35
    • 0022444791 scopus 로고
    • The oxime was prepared by a similar method for dicyclohexylidene congener of 4, see: (a) Iida, H.; Kasahara, K.; Kibayashi, C. J. Am. Chem. Soc. 1986, 108, 4647-4648.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4647-4648
    • Iida, H.1    Kasahara, K.2    Kibayashi, C.3
  • 37
    • 0030755381 scopus 로고    scopus 로고
    • It is known that addition reaction of N-benzyl congener of 6d with 7 in the presence of TMSOTf gives four stereoisomers of adduct with very low stereoselectivity. The stereoselectivity of the present reaction of 6d, therefore, may be mainly due to the effect of the sugar auxiliary. See: Degiorgis, F.; Lombardo, M.; Trombini, C. Tetrahedon 1997, 53, 11721-11730.
    • (1997) Tetrahedon , vol.53 , pp. 11721-11730
    • Degiorgis, F.1    Lombardo, M.2    Trombini, C.3
  • 38
    • 0029994555 scopus 로고    scopus 로고
    • 7c In the present reaction, DATS giving the major isomer 8 would demand that C(4) carbon of 7 should occupy a very close position to the R group of iminium ion B. However, the reaction of nitrone 6 bearing a bulkier R group gave a higher ratio of 8. Consequently, it seems to be reasonable to assume model E for the formation of 8 instead of DAST.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1059-1068
    • Castellari, C.1    Lombardo, M.2    Pietropaolo, G.3    Trombini, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.