메뉴 건너뛰기




Volumn 42, Issue 43, 2003, Pages 5351-5355

Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C by a Carbonyl Ylide Cycloaddition Strategy

Author keywords

Carbonyl ylides; Cycloaddition; Diazo compounds; Metathesis; Total synthesis

Indexed keywords

ADDITION REACTIONS; CATALYSIS; ENZYME INHIBITION; ESTERS; ISOMERS; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 0344875710     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352629     Document Type: Article
Times cited : (64)

References (55)
  • 5
    • 0006722111 scopus 로고
    • For reviews, see: a) U. Koert, Angew. Chem. 1995,107, 849-855; Angew. Chem. Int. Ed. Engl. 1995, 34, 773-778;
    • (1995) Angew. Chem. , vol.107 , pp. 849-855
    • Koert, U.1
  • 6
    • 33748224853 scopus 로고
    • For reviews, see: a) U. Koert, Angew. Chem. 1995,107, 849-855; Angew. Chem. Int. Ed. Engl. 1995, 34, 773-778;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 773-778
  • 7
    • 0001318902 scopus 로고    scopus 로고
    • b) A. Nadin, K. C. Nicolaou, Angew. Chem. 1996, 108, 1732-1766; Angew. Chem. Int. Ed. Engl. 1996, 35, 1622-1656;
    • (1996) Angew. Chem. , vol.108 , pp. 1732-1766
    • Nadin, A.1    Nicolaou, K.C.2
  • 8
    • 0029785061 scopus 로고    scopus 로고
    • b) A. Nadin, K. C. Nicolaou, Angew. Chem. 1996, 108, 1732-1766; Angew. Chem. Int. Ed. Engl. 1996, 35, 1622-1656;
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1622-1656
  • 12
    • 33748233099 scopus 로고
    • Total synthesis of zaragozic acid A: a) K. C. Nicolaou, A. Nadin, J. E. Leresche, E. W. Yue, S. La Greca, Angew. Chem. 1994, 106, 2312-2313; Angew. Chem. Int. Ed. Engl. 1994, 33, 2190-2191;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2190-2191
  • 16
    • 0034671939 scopus 로고    scopus 로고
    • d) K. Tomooka, M. Kikuchi, K. Igawa, M. Suzuki, P.-H. Keong, T. Nakai, Angew. Chem. 2000, 112, 4676-4679; Angew. Chem. Int. Ed. 2000, 39, 4502-4505.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4502-4505
  • 23
    • 0032582859 scopus 로고    scopus 로고
    • Total synthesis of 6,7-dideoxysqualestatin H5: a) S. F. Martin, S. Naito, J. Org. Chem. 1998, 63, 7592-7593;
    • (1998) J. Org. Chem. , vol.63 , pp. 7592-7593
    • Martin, S.F.1    Naito, S.2
  • 25
    • 0025108625 scopus 로고
    • A. Padwa, G. E. Fryxell, L. Zhi, J. Am. Chem. Soc. 1990, 112, 3100-3109. For a copper-catalyzed reaction, see: T. Ibata, K. Jitsuhiro, Bull. Chem. Soc. Jpn. 1979, 52, 3582-3585.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 3100-3109
    • Padwa, A.1    Fryxell, G.E.2    Zhi, L.3
  • 26
    • 0025108625 scopus 로고
    • A. Padwa, G. E. Fryxell, L. Zhi, J. Am. Chem. Soc. 1990, 112, 3100-3109. For a copper-catalyzed reaction, see: T. Ibata, K. Jitsuhiro, Bull. Chem. Soc. Jpn. 1979, 52, 3582-3585.
    • (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 3582-3585
    • Ibata, T.1    Jitsuhiro, K.2
  • 30
    • 0033565006 scopus 로고    scopus 로고
    • For recent studies on the synthesis of bioactive molecules by a carbonyl ylide cycloaddition strategy, see: a) C. S. Straub, A. Padwa, Org. Lett. 1999, 1, 83-85;
    • (1999) Org. Lett. , vol.1 , pp. 83-85
    • Straub, C.S.1    Padwa, A.2
  • 34
    • 0037012683 scopus 로고    scopus 로고
    • d) T. Graening, W. Friedrichsen, J. Lex, H.-G. Schmalz, Angew. Chem. 2002, 114, 1594-1597; Angew. Chem. Int. Ed. 2002, 41, 1524-1526.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1524-1526
  • 36
    • 0027941935 scopus 로고
    • For a carbonyl ylide cycloaddition approach to L-740,758, a product of the oxidative photodegradation of zaragozic acid A, see: H. Koyama, R. G. Ball, G. D. Berger, Tetrahedron Lett. 1994, 35, 9185-9188.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9185-9188
    • Koyama, H.1    Ball, R.G.2    Berger, G.D.3
  • 37
    • 0030600124 scopus 로고    scopus 로고
    • For synthetic studies of zaragozic acids by a carbonyl ylide cycloaddition-rearrangement strategy, see: a) D. M. Hodgson, J. M. Bailey, T. Harrison, Tetrahedron Lett. 1996, 37, 4623-4626;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4623-4626
    • Hodgson, D.M.1    Bailey, J.M.2    Harrison, T.3
  • 42
    • 0344439347 scopus 로고    scopus 로고
    • note
    • 2O, 64%, 3.2:1; toluene, 62%, 4.3:1.
  • 43
    • 0344008073 scopus 로고    scopus 로고
    • note
    • The following dipolarophiles gave the corresponding cycloadducts: methyl propiolate, 75%; methyl vinyl ketone, 59%; methyl acrylate, 68 %; acrylonitrile, 62 %.
  • 44
    • 0345302371 scopus 로고    scopus 로고
    • note
    • 4, 72%.
  • 45
    • 0344008072 scopus 로고    scopus 로고
    • note
    • 1H NOE correlation (18%) between C3-H and C6-H.
  • 46
    • 0000091929 scopus 로고
    • 2 in THF was reported to be effective for the diastereoselective reduction of β-ketosulfoxides: G. Solladié, G. Demailly, C. Greck, Tetrahedron Lett. 1985, 26, 435-438.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 435-438
    • Solladié, G.1    Demailly, G.2    Greck, C.3
  • 51
    • 0038567454 scopus 로고    scopus 로고
    • H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. For a review, see: S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968; Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
    • (2003) Angew. Chem. , vol.115 , pp. 1944-1968
    • Connon, S.J.1    Blechert, S.2
  • 52
    • 0038215596 scopus 로고    scopus 로고
    • H. E. Blackwell, D. J. O'Leary, A. K. Chatterjee, R. A. Washenfelder, D. A. Bussmann, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 58-71. For a review, see: S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968; Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1900-1923
  • 53
    • 0344008071 scopus 로고    scopus 로고
    • note
    • 2. mCPBA = 3-chloroperoxybenzoic acid, TFAA = trifluoroacetic anhydride.
  • 55
    • 0141518449 scopus 로고    scopus 로고
    • Since ruthenium byproducts act as poisons for the following hydrogenation, these impurities were removed by treatment with activated carbon: J. H. Cho, B. M. Kim, Org. Lett. 2003, 5, 531-533.
    • (2003) Org. Lett. , vol.5 , pp. 531-533
    • Cho, J.H.1    Kim, B.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.