메뉴 건너뛰기




Volumn 71, Issue 18, 2006, Pages 6776-6784

Conjugate additions of sulfur-stabilized anions to unsaturated lactams. Synthesis of polyfunctionalized benzo[a]quinolizinone systems

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALKYLATION; NEGATIVE IONS; STEREOCHEMISTRY; SUGARS; SYNTHESIS (CHEMICAL);

EID: 33750459862     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060903w     Document Type: Article
Times cited : (26)

References (80)
  • 1
    • 77956789934 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • Fujii, T.; Ohba, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 51, pp 271-323.
    • (1998) The Alkaloids , vol.51 , pp. 271-323
    • Fujii, T.1    Ohba, M.2
  • 5
    • 33750466296 scopus 로고    scopus 로고
    • U.S. Patent Appl. 2005, 0220715
    • (b) Lin, T.-H. U.S. Patent Appl. 2005, 0220715.
    • Lin, T.-H.1
  • 7
    • 33750466974 scopus 로고
    • For a review on cardiotoxicity of emetine and analogues, see: Stephen, P. M. Prin. Card. Toxicol. 1991, 331-346.
    • (1991) Prin. Card. Toxicol. , pp. 331-346
    • Stephen, P.M.1
  • 20
    • 0003143038 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Exeter
    • (c) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Exeter, 1995; Vol. 11, pp 66-92.
    • (1995) Comprehensive Organometallic Chemistry II , vol.11 , pp. 66-92
    • Gray, M.1    Tinkl, M.2    Snieckus, V.3
  • 26
    • 0037503118 scopus 로고    scopus 로고
    • Rappoport, Z.; Ed.; Patai Series: The Chemistry of Functional Groups; Wiley: Chichester
    • (i) Rappoport, Z.; Marek, I.; In The Chemistry of Organolithium Compounds; Rappoport, Z.; Ed.; Patai Series: The Chemistry of Functional Groups; Wiley: Chichester, 2004.
    • (2004) The Chemistry of Organolithium Compounds
    • Rappoport, Z.1    Marek, I.2
  • 28
    • 46549103031 scopus 로고
    • For reviews on N-acyliminium ion chemistry, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
    • (1985) Tetrahedron , vol.41 , pp. 4367-4416
    • Speckamp, W.N.1    Hiemstra, H.2
  • 29
    • 77957077000 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, pp 271-339.
    • (1988) The Alkaloids , vol.32 , pp. 271-339
    • Hiemstra, H.1    Speckamp, W.N.2
  • 30
    • 0001673091 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (c) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1047-1082.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 31
    • 0001513757 scopus 로고    scopus 로고
    • Workbench ed. E21; Helmchen, G., Hoffmann, R. W., Muzler, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (d) de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis [Houben-Weyl], Workbench ed. E21; Helmchen, G., Hoffmann, R. W., Muzler, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, pp 1952-2010.
    • (1996) Stereoselective Synthesis [Houben-Weyl] , vol.3 , pp. 1952-2010
    • De Koning, H.1    Speckamp, W.N.2
  • 37
    • 0003573894 scopus 로고
    • Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford
    • (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series; Pergamon Press: Oxford, 1992; Vol. 9.
    • (1992) Conjugate Addition Reactions in Organic Synthesis , vol.9
    • Perlmutter, P.1
  • 40
    • 0000957502 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (d) Yamamguchi, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, pp 1121-1139.
    • (1999) Comprehensive Asymmetric Catalysis I-III , vol.3 , pp. 1121-1139
    • Yamamguchi, M.1
  • 41
  • 49
    • 0002639647 scopus 로고
    • For reviews on synthetic uses of á-lithiodithioacetals, see: (a) Seebach, D. Synthesis 1969, 1, 17-36.
    • (1969) Synthesis , vol.1 , pp. 17-36
    • Seebach, D.1
  • 50
    • 33745507572 scopus 로고
    • (b) Krief, A. Tetrahedron 1980, 36, 2531-2640.
    • (1980) Tetrahedron , vol.36 , pp. 2531-2640
    • Krief, A.1
  • 54
    • 33750444697 scopus 로고    scopus 로고
    • Alicante, Spain, July 7-11. See book of abstracts: communication P-39
    • This work was presented in part at the 7th International Symposium on Carbanion Chemistry (ISCC-7), Alicante, Spain, July 7-11, 2004. See book of abstracts: communication P-39.
    • (2004) 7th International Symposium on Carbanion Chemistry (ISCC-7)
  • 56
    • 33750434943 scopus 로고    scopus 로고
    • note
    • When the reaction was carried out in a larger scale (3 g of 1). it was not possible to control the partial reduction of the imide, and N-(3,4-dimethoxyphenylethyl)-4-hydroxybutyramide was obtained. This hydroxyamide could be oxidized (Swern) to the aldehyde and cyclized with TFA to afford 3a in good overall yield. See Supporting Information.
  • 57
    • 0037968038 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see: (a) Tohma, H.; Kita, Y. Top. Curr. Chem. 2003, 224, 209-248.
    • (2003) Top. Curr. Chem. , vol.224 , pp. 209-248
    • Tohma, H.1    Kita, Y.2
  • 63
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (b) Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1992; Vol. 1, Part 1.
    • (1992) Comprehensive Organic Synthesis , vol.1 , Issue.PART 1
    • Schreiber, S.L.1
  • 64
    • 33750484070 scopus 로고    scopus 로고
    • note
    • COSY, HMQC, and NOESY experiments were used to confirm the structure of 8. The value of the coupling constant among the cyclopropane protons and the NOE enhancement between H-11b and the PhSCH were consistent with the stereochemistry shown in the figure. (Diagram presented)
  • 65
    • 0001077546 scopus 로고
    • The formation of this type of cyclopropane derivatives has been previously reported in the conjugate addition of this sulfur-stabilized carbanion to cyclohexenone. See: (a) Cohen, T.; Yu, L.-C. J. Org. Chem. 1985, 50, 3266.
    • (1985) J. Org. Chem. , vol.50 , pp. 3266
    • Cohen, T.1    Yu, L.-C.2
  • 70
    • 33750446047 scopus 로고    scopus 로고
    • See, ref 12a, p 25
    • See, ref 12a, p 25.
  • 71
    • 33750454540 scopus 로고    scopus 로고
    • see ref 15
    • 3: see ref 15.
  • 75
    • 0037453554 scopus 로고    scopus 로고
    • 3/MeI: Takai, S.; Sawada, N.; Isobe, M. J. Org. Chem. 2003, 68 3225-3231.
    • (2003) J. Org. Chem. , vol.68 , pp. 3225-3231
  • 76
    • 0001144019 scopus 로고
    • Hypervalent iodine compounds such as PIFA [phenyliodine(III)bis- (trifluoroacetate)] have been reported to oxidize sulfur-containing compounds. See, for instance: (a) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287-290.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 287-290
    • Stork, G.1    Zhao, K.2
  • 80
    • 0026314946 scopus 로고
    • Boc-protected isoquinoline 19 was prepared by treatment of commercially available 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline with di-tert-butyl dicarbonate. See: Coppola, G. M. J. Heterocycl. Chem. 1991, 28, 1769-1772.
    • (1991) J. Heterocycl. Chem. , vol.28 , pp. 1769-1772
    • Coppola, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.