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Volumn 6, Issue 8, 2004, Pages 1253-1255

Enantioselective total synthesis of (-)-dehydrobatzelladine C

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; CRAMBESCIDIN; DEHYDROBATZELLADINE C; HYDROXYL GROUP; UNCLASSIFIED DRUG;

EID: 2542471402     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0498141     Document Type: Article
Times cited : (24)

References (32)
  • 1
    • 0036775483 scopus 로고    scopus 로고
    • and earlier reviews in this series
    • For reviews, see: Berlinck, R. G. S. Nat. Prod. Rep. 2002, 19, 617 and earlier reviews in this series.
    • (2002) Nat. Prod. Rep. , vol.19 , pp. 617
    • Berlinck, R.G.S.1
  • 3
    • 0025949243 scopus 로고
    • For the initial reports, see: (a) Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925. (b) Jares-Erijman, E. A.; Sakai, R.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5712.
    • (1991) J. Org. Chem. , vol.56 , pp. 5712
    • Jares-Erijman, E.A.1    Sakai, R.2    Rinehart, K.L.3
  • 7
    • 0037165358 scopus 로고    scopus 로고
    • For total syntheses appearing since the most recent reviews, see; (a) Nagasawa, K.; Georgeiva, A.; Koshino, H.; Nakata, T.; Kita, T.; Hashimoto, Y. Org. Lett. 2002, 4, 177. (b) Ishiwata, T.; Hino, T.; Koshino, H.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Org. Lett. 2002, 4, 2921. (c) Nagasawa, K.; Ishiwata, Y.; Hasimoto, Y.; Nakata, T. Tetrahedron Lett. 2002, 43, 6383. (d) Moore, C. G.; Murphy, P. J.; Williams, H. L.; McGown, A. T.; Smith, N. K. Tetrahedron Lett. 2003, 44, 251.
    • (2002) Org. Lett. , vol.4 , pp. 177
    • Nagasawa, K.1    Georgeiva, A.2    Koshino, H.3    Nakata, T.4    Kita, T.5    Hashimoto, Y.6
  • 8
    • 0042691232 scopus 로고    scopus 로고
    • For total syntheses appearing since the most recent reviews, see; (a) Nagasawa, K.; Georgeiva, A.; Koshino, H.; Nakata, T.; Kita, T.; Hashimoto, Y. Org. Lett. 2002, 4, 177. (b) Ishiwata, T.; Hino, T.; Koshino, H.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Org. Lett. 2002, 4, 2921. (c) Nagasawa, K.; Ishiwata, Y.; Hasimoto, Y.; Nakata, T. Tetrahedron Lett. 2002, 43, 6383. (d) Moore, C. G.; Murphy, P. J.; Williams, H. L.; McGown, A. T.; Smith, N. K. Tetrahedron Lett. 2003, 44, 251.
    • (2002) Org. Lett. , vol.4 , pp. 2921
    • Ishiwata, T.1    Hino, T.2    Koshino, H.3    Hashimoto, Y.4    Nakata, T.5    Nagasawa, K.6
  • 9
    • 0037009731 scopus 로고    scopus 로고
    • For total syntheses appearing since the most recent reviews, see; (a) Nagasawa, K.; Georgeiva, A.; Koshino, H.; Nakata, T.; Kita, T.; Hashimoto, Y. Org. Lett. 2002, 4, 177. (b) Ishiwata, T.; Hino, T.; Koshino, H.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Org. Lett. 2002, 4, 2921. (c) Nagasawa, K.; Ishiwata, Y.; Hasimoto, Y.; Nakata, T. Tetrahedron Lett. 2002, 43, 6383. (d) Moore, C. G.; Murphy, P. J.; Williams, H. L.; McGown, A. T.; Smith, N. K. Tetrahedron Lett. 2003, 44, 251.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6383
    • Nagasawa, K.1    Ishiwata, Y.2    Hasimoto, Y.3    Nakata, T.4
  • 10
    • 0037420994 scopus 로고    scopus 로고
    • For total syntheses appearing since the most recent reviews, see; (a) Nagasawa, K.; Georgeiva, A.; Koshino, H.; Nakata, T.; Kita, T.; Hashimoto, Y. Org. Lett. 2002, 4, 177. (b) Ishiwata, T.; Hino, T.; Koshino, H.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Org. Lett. 2002, 4, 2921. (c) Nagasawa, K.; Ishiwata, Y.; Hasimoto, Y.; Nakata, T. Tetrahedron Lett. 2002, 43, 6383. (d) Moore, C. G.; Murphy, P. J.; Williams, H. L.; McGown, A. T.; Smith, N. K. Tetrahedron Lett. 2003, 44, 251.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 251
    • Moore, C.G.1    Murphy, P.J.2    Williams, H.L.3    McGown, A.T.4    Smith, N.K.5
  • 25
    • 2542503065 scopus 로고    scopus 로고
    • note
    • 12 (15) These reactions either returned 12 or resulted in the formation of intractable mixtures.
  • 26
    • 0034518876 scopus 로고    scopus 로고
    • There are several examples of the conversion of simple Biginelli adducts to pyrimidines; see: (a) Kappe, O. C. Acc. Chem. Res. 2000, 33, 879.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 879
    • Kappe, O.C.1
  • 29
    • 2542504045 scopus 로고    scopus 로고
    • note
    • For the preparation of the enantiomer of 17, see ref 8a.
  • 30
    • 2542463638 scopus 로고    scopus 로고
    • note
    • Tethered Biginelli adduct 18 could be isolated in pure form (48% yield) by preparative reverse-phase HPLC.
  • 31
    • 2542444033 scopus 로고    scopus 로고
    • note
    • This oxidation can also be accomplished in similar yield with benzoyl peroxide; however, purification of the product is more cumbersome.
  • 32
    • 2542483178 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of authentic dehydrobatzelladine C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.