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Volumn 69, Issue 8, 2004, Pages 2773-2784

Synthesis of (±)-Hamigeran B, (-)-Hamigeran B, and (±)-1-epi-Hamigeran B: Use of Bulky Silyl Groups to Protect a Benzylic Carbon-Oxygen Bond from Hydrogenolysis

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS; HYDROGENATION; OXYGEN; SYNTHESIS (CHEMICAL);

EID: 1842689009     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030347v     Document Type: Article
Times cited : (45)

References (47)
  • 14
    • 85085783571 scopus 로고    scopus 로고
    • note
    • 3.
  • 19
    • 0002519349 scopus 로고
    • (c) Examples of hydrogenation of tetrasubstituted double bonds conjugated with benzene rings are known (Beilstein database); see, especially: Gray, A. C. G.; Hart, H. J. Am. Chem. Soc. 1968, 90, 2569-2578.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2569-2578
    • Gray, A.C.G.1    Hart, H.2
  • 20
    • 1842655761 scopus 로고    scopus 로고
    • note
    • Based on observation of NOE effects (see Supporting Information).
  • 21
    • 85085784132 scopus 로고    scopus 로고
    • note
    • 1H NMR signals at ca. δ 5 for the benzylic CH-O.
  • 23
    • 1842806897 scopus 로고    scopus 로고
    • note
    • It is believed that hydrogenolysis is facilitated by development of a partial positive charge on the benzylic carbon;18 siloxy groups have a lowered ability to stabilize an adjacent positive charge.20
  • 26
    • 0000449913 scopus 로고
    • Reviews on construction of quaternary centers: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460.
    • (1980) Tetrahedron , vol.36 , pp. 419-460
    • Martin, S.F.1
  • 27
    • 0001521888 scopus 로고
    • (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 30
    • 0033597970 scopus 로고    scopus 로고
    • (e) See also: Sannigrahi, M. Tetrahedron 1999, 55, 9007-9071.
    • (1999) Tetrahedron , vol.55 , pp. 9007-9071
    • Sannigrahi, M.1
  • 38
    • 1842806898 scopus 로고    scopus 로고
    • note
    • Made from 2,5-dimethylphenol by the method of ref 30, except that the formyl group was best generated by benzylic bromination,31 followed by oxidation with DMSO.32


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.