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Volumn 13, Issue 24, 2011, Pages 6444-6447

Total synthesis of the photoprotecting dipyrrolobenzoquinone (+)-terreusinone

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; BIOLOGICAL PRODUCT; GOLD; PYRROLE DERIVATIVE; SUNSCREEN; TERREUSINONE;

EID: 84055223995     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2027398     Document Type: Article
Times cited : (35)

References (75)
  • 9
    • 84055166746 scopus 로고
    • Fischer
    • Previous syntheses of pyrrolo[2, 3-f]indoles (B) rely on classical indolization reactions, see: Japp-Murray: (a) Yamashkin, S. A. Khim. Geterotsikl. Soedin. 1995, 55-57. Fischer:
    • (1995) Khim. Geterotsikl. Soedin. , pp. 55-57
    • Yamashkin S, A.1
  • 16
    • 33744870975 scopus 로고    scopus 로고
    • (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. For the use of achiral and racemic propargylic alcohols in the Larock indolization:
    • (1998) J. Org. Chem. , vol.63 , pp. 7652-7662
    • Larock, R.C.1    Yum, E.K.2    Refvik, M.D.3
  • 37
    • 84055204934 scopus 로고    scopus 로고
    • As the synthesis of aromatic bromides is generally more facile than that of iodides, dibromide 3c was chosen over the diiodide
    • As the synthesis of aromatic bromides is generally more facile than that of iodides, dibromide 3c was chosen over the diiodide.
  • 45
    • 84055214363 scopus 로고    scopus 로고
    • Model studies indicated that triisopropylsilyl protected alkynol 4c was the best substrate for the Larock indolization
    • Model studies indicated that triisopropylsilyl protected alkynol 4c was the best substrate for the Larock indolization.
  • 47
    • 84055166743 scopus 로고    scopus 로고
    • See Supporting Information for full details
    • See Supporting Information for full details.
  • 49
    • 0142099039 scopus 로고    scopus 로고
    • There is only one example of a Larock indolization proceeding with complete reversal in regioselectivity: Nishikawa, T.; Wada, K.; Isobe, M. Biosci. Biotechnol. Biochem. 2002, 66, 2273-2278.
    • (2002) Biosci. Biotechnol. Biochem. , vol.66 , pp. 2273-2278
    • Nishikawa, T.1    Wada, K.2    Isobe, M.3
  • 58
    • 79955900610 scopus 로고    scopus 로고
    • and ensuing references
    • Recent reviews: (a) Toste, F. D. Beil. J. Org. Chem. 2011, 7, 553-554 and ensuing references.
    • (2011) Beil. J. Org. Chem. , vol.7 , pp. 553-554
    • Toste, F.D.1
  • 61
    • 58949093398 scopus 로고    scopus 로고
    • 1757 and ensuing references
    • (d) Gagosz, F. Tetrahedron 2009, 65, 1757 and ensuing references.
    • (2009) Tetrahedron , vol.65
    • Gagosz, F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.