Zincke-Bradsher convergent strategy for the synthesis of the ABE tricyclic core of Manzamine A

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 837-840

  Magnier, Emmanuel ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 NAPHTHYRIDINE; ALKALOID; ALKENE; MANYGEEN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CONTROLLED STUDY; DRUG PURIFICATION; DRUG SYNTHESIS; EXTRACTION; NONHUMAN;

EID: 0032546112     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10744-4     Document Type: Article

References (42)

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33. 8) Compounds 7a and 7b were obtained in low yields with unidentified secondary compounds. These side reactions which are due to the particular reactivity of 2,7-naphthyridinium salts were not observed with isoquinoleinium salt.
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35. 2/MeOH 95:5) affording pure 8b (0.28g, 25% from 5).
36. 3, R = 10.357, ωR = 10.857, for 650 observed reflections. Intensity data were collected on a ENRAF-NONIUS CAD-4 diffractometer.
37. 12) In contrast to our previous study (ref. 4), compound 9 was also unreactive in the presence of BrCN.
38. 13) a) For a review concerning carbon-carbon coupling by metathesis see: a) Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. 1997, 36, 2037-2056.
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40. c) For previous uses of metathesis in Manzamine A synthetic approaches, see references 2j and 2k.
41. 14) For molybdenum catalyst efficient for nitrogen ring closure, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
42. 13C NMR is charaterized by the presence of four signals at 128.4, 128.1, 126.0 and 125.4.