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Volumn 64, Issue 19, 1999, Pages 7184-7201

Total synthesis of michellamines A-C, korupensamines A-D, and ancistrobrevine B

Author keywords

[No Author keywords available]

Indexed keywords

ANCISTROBREVINE B; ANTIRETROVIRUS AGENT; BENZENE DERIVATIVE; FURAN DERIVATIVE; HYDROGEN; KORUPENSAMINE A; KORUPENSAMINE B; KORUPENSAMINE C; KORUPENSAMINE D; MICHELLAMINE A; MICHELLAMINE B; MICHELLAMINE C; NAPHTHALENE DERIVATIVE; PALLADIUM; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033578932     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9908187     Document Type: Article
Times cited : (68)

References (59)
  • 7
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    • The naphthyl isoquinoline alkaloids
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    • (a) Bringmann, G. The Naphthyl Isoquinoline Alkaloids. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 29, Chapter 3.
    • (1986) The Alkaloids , vol.29
    • Bringmann, G.1
  • 8
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    • The naphthylisoquinoline alkaloids
    • Cordell, G., Ed.; Academic Press: New York, Chapter 4
    • (b) Bringmann, G.; Pokorny, F. The Naphthylisoquinoline Alkaloids. In The Alkaloids; Cordell, G., Ed.; Academic Press: New York, 1995; Vol. 46, Chapter 4.
    • (1995) The Alkaloids , vol.46
    • Bringmann, G.1    Pokorny, F.2
  • 13
    • 0344170099 scopus 로고    scopus 로고
    • note
    • Compound supply was problematic, since the only known natural source was the rare A. korupensis liana, which is found only in a limited region of the Cameroonian rainforest.
  • 25
    • 0344601740 scopus 로고    scopus 로고
    • note
    • 12b
  • 33
    • 0345463733 scopus 로고    scopus 로고
    • note
    • For example, cycloaddition of benzyne i (derived from iodotriflate ii by treatment with n-BuLi) with 4-(2-furyl)anisole (iii) gave the undesired regioisomer iv as the only product. We also examined the cycloaddition of benzyne i with THIQ substituted furan v. However, no cycloaddition products were observed, probably because of the hindered nature of v. equation presented
  • 35
    • 0345032656 scopus 로고    scopus 로고
    • note
    • Modifications included changing the number of equivalents of dialkylamide anion, the order and rate of addition, the number of equivalents of dibromide precursor, the solvent, the structure of the dialkylamide base, and the temperature of benzyne generation and reaction. n-Butyllithium was used for the preliminary deprotonation of β,β-dimethyl-N,N-diethylacrylamide (in an attempt to reduce the amount of isopropylcyclohexylamine and the amount of amine-trapped product 19). However, none of these modifications resulted in significant changes in the yield or ratio of products.
  • 40
    • 0344601736 scopus 로고    scopus 로고
    • note
    • 12f The resulting 6,8-dihydrory-N-benzylated THIQ (ix.) was converted efficiently to ent-22. equation presented
  • 42
    • 0345463726 scopus 로고    scopus 로고
    • note
    • While the diastereoselectivity favoring the indicated C(1)-epimer of 38 was only 88% de when the reaction was performed at rt, it rose to 96% de for samples arising from reactions begun at -78 °C and then slowly warmed to rt.
  • 48
    • 0344601734 scopus 로고    scopus 로고
    • note
    • 3, ether, RT) and displacement with potassium cyanide (aqueous ethanol, reflux).
  • 49
    • 33748605775 scopus 로고
    • For a review describing the use of chiral aziridines in synthesis, see: Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 599
    • Tanner, D.1
  • 50
    • 0344170075 scopus 로고    scopus 로고
    • note
    • We appreciate Professor Bruce H. Lipshutz sharing his group's expertise in surmounting this problem.
  • 53
    • 0344601730 scopus 로고    scopus 로고
    • note
    • The acetate analogue of 49 (xiii) was once prepared by coupling the naphthyl triflate xi with the THIQ boronic acid xii. The triflate was derived from the naphthalene-1,4-diol i, which in turn could be prepared by the indicated Diels-Alder reactions. This strategy was inferior to the THIQ-halide/naphthalene-metal routes we adopted (Chart 1) because the synthesis of x was not efficient and the generation of boronic acid xii made the sequence less convergent with respect to the more complex THIQ unit. equation presented
  • 58
    • 0345032639 scopus 로고    scopus 로고
    • note
    • The 4-aryl-substituted 1-naphthol (Ar = 2,4-dimethoxy-6-methylphenyl) xiv was readily coupled by silver oxide to the indigo-blue cross-ring quinone xv and then reduced to the binaphthol derivative xvi. equation presented
  • 59
    • 0024578841 scopus 로고
    • Assays were performed under the Developmental Therapeutics Program at the National Cancer Institute. Protection of CEM-SS cells toward infection by HIV-1 was monitored by quantifying the number of viable cells using XTT/formazin colorimetric detection. Weislow, O. W.; Kiser, R.; Fine, D.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer Inst. 1989, 81, 577.
    • (1989) J. Natl. Cancer Inst. , vol.81 , pp. 577
    • Weislow, O.W.1    Kiser, R.2    Fine, D.3    Bader, J.4    Shoemaker, R.H.5    Boyd, M.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.