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Volumn 64, Issue 1, 1999, Pages 16-22

A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKALOID; ALUMINUM OXIDE; CUPRIC CHLORIDE; DISCORHABDIN C; DISCORHABDIN E; HYDROGEN; IMINE; OXYGEN; PRIANOSIN D; TRIETHYLAMINE; TYRAMINE; UNCLASSIFIED DRUG;

EID: 0033534552     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9815397     Document Type: Article
Times cited : (72)

References (68)
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  • 45
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    • (1957) Free Radicals in Solution , pp. 457-461
    • Walling1
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    • Cherif, M.; Cotelle, P.; Catteau, J. P. Heterocycles 1992, 34, 1749. We discovered discrepancies between the reported characterization data and our data. For full experimental details and full characterization data, please refer to the Supporting Information. For alternate routes to 4,7-dimethoxyindole, see: (a) Rodighiero, G.; Malesani, G.; Fornasiero, U. Gazz. Chim. Ital. 1961, 91, 742.
    • (1992) Heterocycles , vol.34 , pp. 1749
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  • 49
    • 0008885901 scopus 로고
    • Cherif, M.; Cotelle, P.; Catteau, J. P. Heterocycles 1992, 34, 1749. We discovered discrepancies between the reported characterization data and our data. For full experimental details and full characterization data, please refer to the Supporting Information. For alternate routes to 4,7-dimethoxyindole, see: (a) Rodighiero, G.; Malesani, G.; Fornasiero, U. Gazz. Chim. Ital. 1961, 91, 742.
    • (1961) Gazz. Chim. Ital. , vol.91 , pp. 742
    • Rodighiero, G.1    Malesani, G.2    Fornasiero, U.3
  • 53
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    • (e) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. A similiar tryptamine system was reported concurrently with this work in the following: Zhang, H. C.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 1804.
    • (1997) J. Org. Chem. , vol.62 , pp. 1804
    • Zhang, H.C.1    Maryanoff, B.E.2
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    • note
    • 2 and CH=CH groups are rather similar sterically, both enantiomers can occupy the same sites in the crystal cell, albeit with unequal populations.
  • 67
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    • note
    • In the conformation depicted in Scheme 9, it appears that an axial bromide is not in a position to undergo nucleophilic displacement by the imine nitrogen. However, another conformation that brings the halogenated carbon into good proximity for displacement appears to be easily available.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.