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Volumn 52, Issue 3, 1998, Pages 104-111

Desymmetrisation of dienylsilanes. Stereoselective access to cyclitols and carba-sugars

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EID: 0000149724     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (24)

References (78)
  • 1
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    • Aminocyclitol antibiotics
    • American Chemical Society, Washington D.C.
    • a) K.L. Rinehart, T. Suami, 'Aminocyclitol antibiotics', Symposium Series, No. 125, American Chemical Society, Washington D.C., 1980;
    • (1980) Symposium Series , vol.125
    • Rinehart, K.L.1    Suami, T.2
  • 32
    • 84943847437 scopus 로고
    • 2: K.A. Andrianov, N.V. Delazari, Dokl. Akad. Nauk. SSSR 1958, 122, 393 (Chem. Abstr. 1959, 53, 2133).
    • (1959) Chem. Abstr. , vol.53 , pp. 2133
  • 33
    • 0041396332 scopus 로고    scopus 로고
    • note
    • It is noteworthy that the second dihydroxylation occurred exclusively syn relative to the silicon group.
  • 34
    • 85128572654 scopus 로고    scopus 로고
    • note
    • 1H-NMR of Mosher's esters prepared from alcohol 8.
  • 35
    • 0042899439 scopus 로고    scopus 로고
    • note
    • When epoxidation was carried out using (+)-DET ((+)-diethyl tartrate), the conversion was complete after only 4 d, illustrating the important difference in reactivity between the 'matched' and the 'mis-matched' pair.
  • 43
    • 0000640476 scopus 로고
    • Two enantioselective syntheses of (+)-palitantin ((+)-14) have been reported to date and were found to be less efficient in term of yields and number of steps [22]: S. Hanessian, Y. Sakito, D. Dhanoa, L. Baptistella, Tetrahedron 1989, 45, 6623.
    • (1989) Tetrahedron , vol.45 , pp. 6623
    • Hanessian, S.1    Sakito, Y.2    Dhanoa, D.3    Baptistella, L.4
  • 45
    • 0000269981 scopus 로고
    • The ring epoxide opening followed a transdiaxial mode, thus obeying the Fürst-Plattner rule: A. Fürst, P.A. Plattner, Helv. Chim. Acta 1949, 32, 275.
    • (1949) Helv. Chim. Acta , vol.32 , pp. 275
    • Fürst, A.1    Plattner, P.A.2
  • 56
    • 0004121735 scopus 로고
    • Eds. U. Umezawa and I.R. Hooper, Springer, Berlin
    • I.R. Hooper, in 'Aminoglycoside Antibiotics', Eds. U. Umezawa and I.R. Hooper, Springer, Berlin, 1982, p. 7.
    • (1982) Aminoglycoside Antibiotics , pp. 7
    • Hooper, I.R.1
  • 58
    • 0001009486 scopus 로고
    • and ref. cit. therein
    • a) T. Suami, Top. Curr. Chem. 1990, 154, 257 and ref. cit. therein.
    • (1990) Top. Curr. Chem. , vol.154 , pp. 257
    • Suami, T.1
  • 62
    • 85128584020 scopus 로고    scopus 로고
    • note
    • 4) were carried out, unfortunately leading to complex mixtures.
  • 64
    • 0011388902 scopus 로고
    • For a review on the [2,3]-Wittig rearrangement, see: T. Mikami, T. Nakai, Synthesis 1992, 234.
    • (1992) Synthesis , pp. 234
    • Mikami, T.1    Nakai, T.2
  • 66
    • 0041897295 scopus 로고    scopus 로고
    • note
    • It is worthnoting that Peterson elimination (at C(2)/C(3), 40) did not occur under these conditions.
  • 70
    • 85128548861 scopus 로고    scopus 로고
    • note
    • 2SiCl (3) at low temperature.
  • 73
    • 85128543548 scopus 로고    scopus 로고
    • note
    • 2)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.