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Volumn 70, Issue 20, 2005, Pages 8231-8234

Modular total synthesis of lamellarin D

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; DNA TOPOISOMERASE; LAMELLARIN D; LAMELLARIN DERIVATIVE; METHYL 5,6 DIHYDROPYRROLO[2,1 ALPHA]ISOQUINOLINE 2 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

EID: 25444485227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051083a     Document Type: Article
Times cited : (115)

References (22)
  • 2
    • 77956687883 scopus 로고    scopus 로고
    • Gribble, G. W., Joule, J. A., Eds.; Pergamon: Oxford, UK
    • For a recent review, see: Cironi, P.; Albericio, F.; Álvarez, M. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Pergamon: Oxford, UK, 2004; Vol. 16, pp 1.
    • (2004) Progress in Heterocyclic Chemistry , vol.16 , pp. 1
    • Cironi, P.1    Albericio, F.2    Álvarez, M.3
  • 9
    • 1342313703 scopus 로고
    • Methyl pyrrole-2-carboxylate was obtained from pyrrole by acylation with trichloroacetyl chloride as described by Harbuck, J. W.; Rapoport, H. J. Org. Chem. 1972, 37, 3618. The 2-trichloroacetylpyrrole was treated with a solution of NaOMe in MeOH at 0 °C to furnish the methyl ester.
    • (1972) J. Org. Chem. , vol.37 , pp. 3618
    • Harbuck, J.W.1    Rapoport, H.2
  • 10
    • 3342885342 scopus 로고    scopus 로고
    • Tosylate 4 was obtained from the 2-bromo-5-isopropoxy-4- methoxybenzaldehyde as detailed in Supporting Information. A Wittig reaction afforded the styrene, while anti-Markovnikov hydroboration and standard tosylation of the resulting 2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethanol gave 4. Preparation of 2-(2-bromo-5-isopropoxy-4-methoxyphenyl) ethanol was described from the same benzaldehyde using a different procedure by: Treu, M.; Jordis, U. Molecules 2002, 7, 374.
    • (2002) Molecules , vol.7 , pp. 374
    • Treu, M.1    Jordis, U.2
  • 11
    • 25444433488 scopus 로고    scopus 로고
    • note
    • 13C NMR.
  • 12
    • 25444433987 scopus 로고    scopus 로고
    • note
    • 1H NMR. The reaction could be followed by HPLC.
  • 14
    • 25444493018 scopus 로고    scopus 로고
    • note
    • Obtained from 3-isopropoxy-4-methoxybenzaldehyde by Baeyer-Villiger reaction followed by protection of the resulting phenol and bromination; see Supporting Information for details.
  • 18
    • 25444451482 scopus 로고    scopus 로고
    • note
    • 2 and DPEphos afforded the debrominated compound, 2,4-diisopropoxy-1-methoxybenzene, instead of the desired building block 11b.
  • 19
    • 25444480403 scopus 로고    scopus 로고
    • note
    • 2 in refluxing toluene or pyridine, or (iii) Pd-C in toluene or decalin were unsuccessful (unpublished results).
  • 20
    • 0141743523 scopus 로고    scopus 로고
    • Protection of phenol groups as isopropoxyethers was previously demonstrated to be very efficient in the solid-phase synthesis of lamellarins: Cironi, P.; Manzanares, I.; Albericio, F.; Álvarez, M. Org. Lett. 2003, 5, 2959.
    • (2003) Org. Lett. , vol.5 , pp. 2959
    • Cironi, P.1    Manzanares, I.2    Albericio, F.3    Álvarez, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.