Total synthesis of (+)-aloperine. Use of a nitrogen-bound silicon tether in an intramolecular Dieis-Alder reaction

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 700-709

  Brosius, Arthur D ^a   Overman, Larry E ^a,b   Schwink, Lothar ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKALOID DERIVATIVE; ALOPERINE; LUPININE; N ALLYLALOPERINE; N METHYLALOPERINE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033518612     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983013+     Document Type: Article

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75. 35
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81. The authors have deposited atomic coordinates for 68 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 23 Union Road, Cambridge, CB2 1EZ, UK.
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83. 2 at atmospheric pressure. Other general experimental details have been described: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
84. An improved preparation of this known compound is described in the Supporting Information.