메뉴 건너뛰기




Volumn 48, Issue 19, 2009, Pages 3444-3448

Total synthesis and absolute configuration of the bisanthraquinone antibiotic BE-43472B

Author keywords

Anthraquinones; Antibiotics; Cascade reactions; Diels alder reactions; Total synthesis

Indexed keywords

ABSOLUTE CONFIGURATION; ANTHRAQUINONES; CASCADE REACTIONS; DIELS-ALDER REACTION; DIELS-ALDER REACTIONS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 70349977037     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900058     Document Type: Article
Times cited : (48)

References (45)
  • 1
    • 70349940511 scopus 로고    scopus 로고
    • Antitumoric BE-43472 manufacture with streptomyces: H. Kushida, S. Nakajima, T. Koyama, H. Suzuki, K. Ojiri, H. Suda, JP 08143569,1996.
    • "Antitumoric BE-43472 manufacture with streptomyces": H. Kushida, S. Nakajima, T. Koyama, H. Suzuki, K. Ojiri, H. Suda, JP 08143569,1996.
  • 4
    • 47749093130 scopus 로고    scopus 로고
    • For recent reviews on this topic, see: a
    • For recent reviews on this topic, see: a) G. Taubes, Science 2008, 321, 356.
    • (2008) Science , vol.321 , pp. 356
    • Taubes, G.1
  • 5
    • 70349938890 scopus 로고    scopus 로고
    • K. C. Nicolaou, J. S. Chen, D. J. Edmonds, A. A. Estrada, Angew. Chem. 2009, 121, 670; Angew. Chem. Int. Ed. 2009, 48, 660.
    • b) K. C. Nicolaou, J. S. Chen, D. J. Edmonds, A. A. Estrada, Angew. Chem. 2009, 121, 670; Angew. Chem. Int. Ed. 2009, 48, 660.
  • 6
    • 70349937245 scopus 로고    scopus 로고
    • For previous synthetic studies inspired by BE-43472B, see: a K. Suzuki, H. Takikawa, Y. Hachisu, J. W. Bode, Angew. Chem. 2007, 119, 3316;
    • For previous synthetic studies inspired by BE-43472B, see: a) K. Suzuki, H. Takikawa, Y. Hachisu, J. W. Bode, Angew. Chem. 2007, 119, 3316;
  • 8
    • 70349963812 scopus 로고    scopus 로고
    • H. Takikawa, K. Hikita, K. Suzuki, Angew. Chem. 2008, 120, 10035 Angew. Chem. Int. Ed. 2008, 47, 9887.
    • b) H. Takikawa, K. Hikita, K. Suzuki, Angew. Chem. 2008, 120, 10035 Angew. Chem. Int. Ed. 2008, 47, 9887.
  • 10
    • 70349938892 scopus 로고    scopus 로고
    • E. J. Corey, Angew. Chem. 2002, 114, 1724; Angew. Chem. Int. Ed. 2002, 41, 1650.
    • b) E. J. Corey, Angew. Chem. 2002, 114, 1724; Angew. Chem. Int. Ed. 2002, 41, 1650.
  • 11
    • 70349960907 scopus 로고    scopus 로고
    • K. C. Nicolaou, Angew. Chem. 2002, 114, 1742; Angew. Chem. Int. Ed. 2002, 41, 1668.
    • K. C. Nicolaou, Angew. Chem. 2002, 114, 1742; Angew. Chem. Int. Ed. 2002, 41, 1668.
  • 19
    • 0000648235 scopus 로고
    • For Diels-Alder reactions with substituted naphthoquinones, see: a
    • For Diels-Alder reactions with substituted naphthoquinones, see: a) B. M. Trost, J. Ippen, W. C. Vladuchick, J. Am. Chem. Soc. 1977, 99, 8116.
    • (1977) J. Am. Chem. Soc , vol.99 , pp. 8116
    • Trost, B.M.1    Ippen, J.2    Vladuchick, W.C.3
  • 24
    • 0003586413 scopus 로고    scopus 로고
    • For a discussion of transition states of Diels-Alder reactions with chiral 1,3-dienes, see a P. G. McDougal, J. M. Jump, C. Rojas, J. G. Rico, Tetrahedron Lett. 1989, 30, 3897
    • For a discussion of transition states of Diels-Alder reactions with chiral 1,3-dienes, see a) P. G. McDougal, J. M. Jump, C. Rojas, J. G. Rico, Tetrahedron Lett. 1989, 30, 3897
  • 27
    • 70349940535 scopus 로고    scopus 로고
    • The rather puzzling exquisite regiochemical outcome of this Diels-Alder reaction cannot be fully explained at this time, and studies directed toward its further understanding are continuing. It should be noted, however, that that a diene corresponding to 4 with a MEM-O group at its C-1 terminus (rather than a TBS-O group at its C-2 position) reacted with dienophile 5 to give exclusively the opposite regioisomeric Diels-Alder product. Further details will be reported in the full account of this work
    • The rather puzzling exquisite regiochemical outcome of this Diels-Alder reaction cannot be fully explained at this time, and studies directed toward its further understanding are continuing. It should be noted, however, that that a diene corresponding to 4 with a MEM-O group at its C-1 terminus (rather than a TBS-O group at its C-2 position) reacted with dienophile 5 to give exclusively the opposite regioisomeric Diels-Alder product. Further details will be reported in the full account of this work.
  • 28
    • 70349951500 scopus 로고    scopus 로고
    • An alternative, but less likely, mechanism for the conversion of2 to 22/epi-22 may involve initial oxonium ion formation followed by intramolecular attack from the nearby MeO group and extrusion of MeOH.
    • An alternative, but less likely, mechanism for the conversion of2 to 22/epi-22 may involve initial oxonium ion formation followed by intramolecular attack from the nearby MeO group and extrusion of MeOH.
  • 29
    • 0007260358 scopus 로고    scopus 로고
    • For examples of intermolecular SN(Ar) ipso substitution of a MeO group by carbon nucleophiles, see: a) R. C. Fuson, S. B. Speck, J. Am. Chem. Soc. 1942, 64, 2446
    • N(Ar) ipso substitution of a MeO group by carbon nucleophiles, see: a) R. C. Fuson, S. B. Speck, J. Am. Chem. Soc. 1942, 64, 2446.
  • 33
    • 33947449188 scopus 로고    scopus 로고
    • N(Ar) ipso substitution of a MeO group by an oxygen nucleophile. For the introduction of the term ipso substitution, see:
    • N(Ar) ipso substitution of a MeO group by an oxygen nucleophile. For the introduction of the term ipso substitution, see:
  • 35
    • 70349975095 scopus 로고    scopus 로고
    • Since epimers 22 and epi-22 are hardly separable and because the subsequent intermediates 23 and 24 were also shown to epimerize under the reaction conditions employed for their generation, it was more expedient and efficient to carry the mixture of epi-22 and 22 through the three-step sequence and separate the obtained enone 25 and its C-3 epimer epi-25 by chromatography.
    • Since epimers 22 and epi-22 are hardly separable and because the subsequent intermediates 23 and 24 were also shown to epimerize under the reaction conditions employed for their generation, it was more expedient and efficient to carry the mixture of epi-22 and 22 through the three-step sequence and separate the obtained enone 25 and its C-3 epimer epi-25 by chromatography.
  • 36
    • 70349937272 scopus 로고    scopus 로고
    • CCDC 714178 (25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
    • CCDC 714178 (25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
  • 37
    • 70349938909 scopus 로고    scopus 로고
    • In the initial synthesis of, we also obtained the X-ray crystal structure of ent-25. CCDC 711967 (ent-25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallo- graphic Data Centre via
    • In the initial synthesis of (-we also obtained the X-ray crystal structure of ent-25. CCDC 711967 (ent-25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallo- graphic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 40
    • 70349955874 scopus 로고    scopus 로고
    • Interestingly, the minor epimeric oxirane epi-28 remained unchanged under the same photolytic conditions.
    • Interestingly, the minor epimeric oxirane epi-28 remained unchanged under the same photolytic conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.