Stereocontrolled total syntheses of meso-chimonanthine and meso-calycanthine via a novel samarium mediated reductive dialkylation

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 8166-8167

  Link, J T ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALYCANTHINE; CHIMONANTHINE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029790020     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961757m     Document Type: Article

References (27)

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14. 6a
15. 13C NMR, IR, and MS analysis, while elemental composition was confirmed by combustion analysis or high-resolution mass spectrometry. Yields refer to isolated products purified on silica gel unless noted otherwise. Standard abbreviations employed are defined in: J Org. Chem. 1996, 61, 22A.
16. 4Cl provided both isomers of (N-benzyl)dihydroisoindigo (in 1.5:1 ratio) in 97% yield.
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19. A simple salt effect is not involved, since addition of KCI (instead of LiCl) yielded (N-benzyl)dihydroisoindigo after protonolysis. rather than cyclohexene 7.
20. 2R′). which upon treatment with reducing agents typically lead to a ∼1:1 mixture of oxindole IS and indole 16. equation presented
21. For previous reports of the preparation of similar ring systems, see: (a) Hodson, H. F.; Smith, G. F.; Wróbel, J. T. Chem. Ind. 1958, 1551. (b) Hino, T. Chem. Pharm. Bull. 1961, 9, 988.
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25. 19
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