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Volumn , Issue 11, 2010, Pages 2206-2211

Synthesis of N-Bz-protected D-daunosamine and D-Ristosamine by silica gel promoted intramolecular conjugate addition of trichloroacetimidates obtained from osmundalactone and its epimer

Author keywords

Amino sugars; Heterocycles; Natural products; Nucleophilic addition

Indexed keywords


EID: 77950241808     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901402     Document Type: Article
Times cited : (28)

References (55)
  • 11
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    • A few example of intramolecular conjugate additions of trichloroacetimidates, which were prepared in situ, in a cyclic system were reported: a to α,ß-unsaturated esters
    • A few example of intramolecular conjugate additions of trichloroacetimidates, which were prepared in situ, in a cyclic system were reported: a) to α,ß-unsaturated esters:
  • 14
    • 0001417001 scopus 로고
    • to α,ß-unsaturated sulfones:X. C. Li, P. L. Fuchs, Synlett 1994, 629-630.
    • (1994) Synlett , pp. 629-630
    • Li, X.C.1    Fuchs, P.L.2
  • 15
    • 77950222080 scopus 로고    scopus 로고
    • There are some useful reactions involving trichloroacetimidates for the introduction of a nitrogen functionality; a for electrophile-promoted intramolecular aminations of trichloroacetimidates derived from allylic and homoallylic alcohols, see
    • There are some useful reactions involving trichloroacetimidates for the introduction of a nitrogen functionality; a) for electrophile-promoted intramolecular aminations of trichloroacetimidates derived from allylic and homoallylic alcohols, see:
  • 16
    • 4143050267 scopus 로고    scopus 로고
    • and references cited therein
    • H.-S. Lee, S. H. Kang, Synlett 2004, 1673-1685 and references cited therein
    • (2004) Synlett , pp. 1673-1685
    • Lee, H.-S.1    Kang, S.H.2
  • 17
    • 0000762868 scopus 로고
    • b) for acid-promoted intramolecular epoxide opening of trichloroacetimidates, see: B. Bernet, A. Vasella, Tetrahedron Lett, 1983, 24, 5491-5494;
    • (1983) Tetrahedron Lett , vol.24 , pp. 5491-5494
    • Bernet, B.1    Vasella, A.2
  • 21
    • 33846599336 scopus 로고    scopus 로고
    • and references cited therein
    • and see also C. Rondot, P. Retailleau, J. Zhu, Org. Lett. 2007, 9, 247-250 and references cited therein
    • (2007) Org. Lett. , vol.9 , pp. 247-250
    • Rondot, C.1    Retailleau, P.2    Zhu, J.3
  • 22
    • 0001741549 scopus 로고
    • for Overman, rearrangement, see: L. E. Overman, Acc. Chem. Res. 1980, 13, 218-224.
    • (1980) Acc. Chem. Res. , vol.13 , pp. 218-224
    • Overman, L.E.1
  • 24
    • 55549123832 scopus 로고    scopus 로고
    • For a recent synthesis of 3-amino-2,3,6-trideoxyhexose, see: and references cited therein.
    • For a recent synthesis of 3-amino-2,3,6-trideoxyhexose, see: K. Gregory, G. K. Friestad, T. Jiang, G. M. Fioroni, Tetrahedron 2008, 64, 11549-11557, and references cited therein.
    • (2008) Tetrahedron , vol.64 , pp. 11549-11557
    • Gregory, K.1    Friestad, G.K.2    Jiang, T.3    Fioroni, G.M.4
  • 26
    • 77950271391 scopus 로고    scopus 로고
    • note
    • During our course of pursuing the effective synthesis of osmundalactones, an appealing method for δ-lactonization accompanied by trans/cis isomerization was reported. The mechanism of trans/cis isomerization was suggested to occur by pyridine-assisted addition-elimination in this paper.
  • 33
    • 77950247430 scopus 로고    scopus 로고
    • For a few examples of the use of silica gel in heteroconjugate additions, see: a for addition of amines to α,ß-unsaturated esters and nitriles
    • For a few examples of the use of silica gel in heteroconjugate additions, see: a) for addition of amines to α,ß-unsaturated esters and nitriles:
  • 35
    • 77950209333 scopus 로고    scopus 로고
    • for addition of amines to α,ß-unsaturated amides
    • b) for addition of amines to α,ß-unsaturated amides:
  • 37
    • 77950240777 scopus 로고    scopus 로고
    • for addition of thiols to α,ß-unsaturated ketones
    • for addition of thiols to α,ß-unsaturated ketones:
  • 39
    • 77950199944 scopus 로고    scopus 로고
    • an intramolecular version of the conjugate addition of thioamide to α,ßunsaturated esters or amides to produce thiazolines was reported
    • an intramolecular version of the conjugate addition of thioamide to α,ßunsaturated esters or amides to produce thiazolines was reported:
  • 42
    • 77950258330 scopus 로고    scopus 로고
    • Selected literature on N-Bz-daunosamine synthesis
    • Selected literature on N-Bz-daunosamine synthesis:
  • 49
    • 77950249205 scopus 로고    scopus 로고
    • Selected literature on osmundalactone, which include melting point data: A isolation of osmundarin and osmundalactone
    • Selected literature on osmundalactone, which include melting point data: a) isolation of osmundarin and osmundalactone:
  • 53


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.