An asymmetric route to the conanine BCDE ring system. A formal total synthesis of (+)-conessine

Journal of the American Chemical Society

Volumn 118, Issue 41, 1996, Pages 9876-9883

  Kopach, Michael E ^a   Fray, Andrew H ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CONESSINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029999489     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961903o     Document Type: Article

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72. It is recommended that this procedure be conducted behind a blast shield in a hood.
73. This procedure involved the use of smaller amounts of dipole precursor 8 whereas utilizing the conditions described in the discussion (6 h at 190°C) gave the same yield of product. However, the latter conditions required the use of larger amounts of dipole precursor 8.
74. The X-ray structures have been submitted to the Cambridge Crystallographic Center. The ORTEP structure for 20 is also included in the supporting information.
75. 13C NMR spectrum, recorded at 100°C (toluene), did not show any significant differences, in addition to solvent overlapping with the sample.