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Volumn 9, Issue 2, 2003, Pages 389-399

Total synthesis of the antitumor acetogenin mosin B: Desymmetrization approach to the stereodivergent synthesis of threo/trans/erythro-type acetogenins

Author keywords

Annonaceous acetogenins; Asymmetric desymmetrization; Mosin B; Structure elucidation; Total synthesis

Indexed keywords

CARBON;

EID: 0037455248     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390040     Document Type: Article
Times cited : (27)

References (37)
  • 1
    • 0032891112 scopus 로고    scopus 로고
    • For reviews of annonaceous acetogenins, see: a) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540; b) L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z.-M. Gu, K. He, J. L. McLaughlin. Nat. Prod. Rep. 1996, 13, 275-306; c) J. K. Rupprecht, Y.-H. Hui, J. L. McLaughlin, J. Nat. Prod. 1990, 53, 237-278; d) A. Cavé, B. Figadére, A. Laurens, D. Cortes, Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae, Vol. 70 (Ed.: W. Herz), Springer, New York, 1997, pp. 81-288.
    • (1999) J. Nat. Prod. , vol.62 , pp. 504-540
    • Alali, F.Q.1    Liu, X.-X.2    McLaughlin, J.L.3
  • 2
    • 0030221749 scopus 로고    scopus 로고
    • For reviews of annonaceous acetogenins, see: a) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540; b) L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z.-M. Gu, K. He, J. L. McLaughlin. Nat. Prod. Rep. 1996, 13, 275-306; c) J. K. Rupprecht, Y.-H. Hui, J. L. McLaughlin, J. Nat. Prod. 1990, 53, 237-278; d) A. Cavé, B. Figadére, A. Laurens, D. Cortes, Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae, Vol. 70 (Ed.: W. Herz), Springer, New York, 1997, pp. 81-288.
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 275-306
    • Zeng, L.1    Ye, Q.2    Oberlies, N.H.3    Shi, G.4    Gu, Z.-M.5    He, K.6    McLaughlin, J.L.7
  • 3
    • 0025373035 scopus 로고
    • For reviews of annonaceous acetogenins, see: a) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540; b) L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z.-M. Gu, K. He, J. L. McLaughlin. Nat. Prod. Rep. 1996, 13, 275-306; c) J. K. Rupprecht, Y.-H. Hui, J. L. McLaughlin, J. Nat. Prod. 1990, 53, 237-278; d) A. Cavé, B. Figadére, A. Laurens, D. Cortes, Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae, Vol. 70 (Ed.: W. Herz), Springer, New York, 1997, pp. 81-288.
    • (1990) J. Nat. Prod. , vol.53 , pp. 237-278
    • Rupprecht, J.K.1    Hui, Y.-H.2    McLaughlin, J.L.3
  • 4
    • 0030625527 scopus 로고    scopus 로고
    • (Ed.: W. Herz), Springer, New York
    • For reviews of annonaceous acetogenins, see: a) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540; b) L. Zeng, Q. Ye, N. H. Oberlies, G. Shi, Z.-M. Gu, K. He, J. L. McLaughlin. Nat. Prod. Rep. 1996, 13, 275-306; c) J. K. Rupprecht, Y.-H. Hui, J. L. McLaughlin, J. Nat. Prod. 1990, 53, 237-278; d) A. Cavé, B. Figadére, A. Laurens, D. Cortes, Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae, Vol. 70 (Ed.: W. Herz), Springer, New York, 1997, pp. 81-288.
    • (1997) Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae , vol.70 , pp. 81-288
    • Cavé, A.1    Figadére, B.2    Laurens, A.3    Cortes, D.4
  • 8
    • 0037018447 scopus 로고    scopus 로고
    • and references therein
    • For recent total syntheses of mono-THF acetogenins, see: H. Makabe, Y. Hattori, A. Tanaka, T. Oritani, Org. Lett. 2002, 4, 1083-1085 and references therein.
    • (2002) Org. Lett. , vol.4 , pp. 1083-1085
    • Makabe, H.1    Hattori, Y.2    Tanaka, A.3    Oritani, T.4
  • 20
    • 12244275182 scopus 로고    scopus 로고
    • note
    • In the presence of CuI, the epoxide 18 was opened by iodide to give an iodohydrin rather than the coupling product 19.
  • 24
    • 12244269257 scopus 로고    scopus 로고
    • note
    • In this coupling reaction, we observed a by-product in which SPh was substituted for the iodide.
  • 26
    • 0033615769 scopus 로고    scopus 로고
    • During the course of our study. Kitahara reported another solution employing a less hindered MeS group instead of a PhS group as an anion-stabilizing group: a) W.-Q. Yang, T. Kitahara, Tetrahedron Lett. 1999, 40, 7827-7830; b) W.-Q. Yang, T. Kitahara, Tetrahedron 2000, 56, 1451-1461.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7827-7830
    • Yang, W.-Q.1    Kitahara, T.2
  • 27
    • 0034629033 scopus 로고    scopus 로고
    • During the course of our study. Kitahara reported another solution employing a less hindered MeS group instead of a PhS group as an anion-stabilizing group: a) W.-Q. Yang, T. Kitahara, Tetrahedron Lett. 1999, 40, 7827-7830; b) W.-Q. Yang, T. Kitahara, Tetrahedron 2000, 56, 1451-1461.
    • (2000) Tetrahedron , vol.56 , pp. 1451-1461
    • Yang, W.-Q.1    Kitahara, T.2
  • 34
    • 12244312101 scopus 로고    scopus 로고
    • note
    • Although a 9:1 mixture of (E/Z)-45 isomers was used for the Nozaki -Hiyama - Kishi reaction, the coupling reaction gave only the E allylic alcohol 46 presumably due to E/Z isomerization of the organochromium reagent and the low reactivity of the Z isomer.
  • 36
    • 12244282024 scopus 로고    scopus 로고
    • note
    • 50 value of mosin B against PaCa-2 cells was 72-fold higher than that of adriamycin (ref. [4]). The discrepancy from our results was probably caused by a difference in the passage of cancer cells or in the bioassay protocol. However, we cannot prove this at the present time, since the natural mosin B is not available.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.