메뉴 건너뛰기




Volumn 69, Issue 8, 1996, Pages 2281-2286

Simple Synthesis of trans-α,β-Dibenzyl-γ-butyrolactone Lignans by Diastereoselective Reduction of α-Benzylidene-β-benzyl-γ-butyrolactones Using NaBH4-NiCl2

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; LIGNAN;

EID: 0029789427     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2281     Document Type: Article
Times cited : (21)

References (49)
  • 1
    • 0004069487 scopus 로고
    • Andhra University Press, Andhra Pradesh
    • a) C. B. S. Rao, "Chemistry of Lignans," Andhra University Press, Andhra Pradesh (1978)
    • (1978) Chemistry of Lignans
    • Rao, C.B.S.1
  • 2
    • 0004266767 scopus 로고
    • Cambridge Univ. Press, Cambridge
    • b) D. C. Ayres and J. D. Loike, "Lignans," Cambridge Univ. Press, Cambridge (1990)
    • (1990) Lignans
    • Ayres, D.C.1    Loike, J.D.2
  • 33
    • 84982061569 scopus 로고
    • 1H NMR spectra: See, a) von M. Kuhn and A. von Wartburg, Helv. Chim. Acta, 50, 1546 (1967) b) J. Banerji, B. Das, A. Chatterjee, and J. N. Shoolery, Phytochemistry, 23, 2323 (1984).
    • (1967) Helv. Chim. Acta , vol.50 , pp. 1546
    • Von Kuhn, M.1    Von Wartburg, A.2
  • 37
    • 33845555740 scopus 로고
    • Besides Pfaltz's proposal, three other mechanisms have been proposed, see: a) S. W. Heinzman and B. Ganem, J. Am. Chem. Soc., 104, 6801 (1982) b) M. Narisada, I. Horibe, F. Watanabe, and K. Takeda, J. Org. Chem., 54, 5308 (1989) c) N. Abe, F. Fujisaki, K. Sumoto, and S. Miyano, Chem. Pharm, Bull, 39, 1167 (1991).
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 6801
    • Heinzman, S.W.1    Ganem, B.2
  • 38
    • 0001346254 scopus 로고
    • Besides Pfaltz's proposal, three other mechanisms have been proposed, see: a) S. W. Heinzman and B. Ganem, J. Am. Chem. Soc., 104, 6801 (1982) b) M. Narisada, I. Horibe, F. Watanabe, and K. Takeda, J. Org. Chem., 54, 5308 (1989) c) N. Abe, F. Fujisaki, K. Sumoto, and S. Miyano, Chem. Pharm, Bull, 39, 1167 (1991).
    • (1989) J. Org. Chem. , vol.54 , pp. 5308
    • Narisada, M.1    Horibe, I.2    Watanabe, F.3    Takeda, K.4
  • 39
    • 0025910197 scopus 로고
    • Besides Pfaltz's proposal, three other mechanisms have been proposed, see: a) S. W. Heinzman and B. Ganem, J. Am. Chem. Soc., 104, 6801 (1982) b) M. Narisada, I. Horibe, F. Watanabe, and K. Takeda, J. Org. Chem., 54, 5308 (1989) c) N. Abe, F. Fujisaki, K. Sumoto, and S. Miyano, Chem. Pharm, Bull, 39, 1167 (1991).
    • (1991) Chem. Pharm, Bull , vol.39 , pp. 1167
    • Abe, N.1    Fujisaki, F.2    Sumoto, K.3    Miyano, S.4
  • 46
    • 84889513694 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra with those of the authentic sample of 1 and 1′ that were synthesized by the use of the known methods (It is well documented that benzylation of the β-benzyl-γ-butyrolantones 4 afforded the trans-dibenzyllactones 1 exclusively and hydrogenation of the α-benzylidene-β-benzyl-γ-butyrolantones 3 afforded the cisisomers 1′ exclusively: See, Refs. 3c, 3d, 3e, and 3f).
  • 47
    • 0002724863 scopus 로고
    • MOPAC Ver. 5, J. J. P. Stewart, QCPE #455; Revised as Ver. 5.01 by T. Hirano, for UNIX machines, JCPE Newsletter, 1(2), 36 (1989).
    • (1989) JCPE Newsletter , vol.1 , Issue.2 , pp. 36
    • Hirano, T.1
  • 48
    • 84889559374 scopus 로고    scopus 로고
    • TRIPOS, Inc., 1699 S. Hanley Road, St. Louis, Missouri 63144-2913
    • TRIPOS, Inc., 1699 S. Hanley Road, St. Louis, Missouri 63144-2913.
  • 49
    • 0025253529 scopus 로고
    • Takahashi and Tsuji reported that the stereoselectivity observed in protonation of the metal enolate of 3-alkyl-2-methyl-1-acetylcyclopentene, prepared by conjugate addition of vinyl group, could be rationalized by MM2 calculations. They fixed the position of the proton donor 2.5 Å above or below the α-carbon of the metal enolate, and optimized the geometry for the rest of the system: H. Yamada, K. Shimizu, M. Nisar, T. Takahashi, and J. Tsuji, Tetrahedron Lett., 31, 2407 (1990).
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2407
    • Yamada, H.1    Shimizu, K.2    Nisar, M.3    Takahashi, T.4    Tsuji, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.