Iodine-induced cyclizations of N-alkoxyaminoalkenes. A stereocontrolled approach to trans-2,6-disubstituted piperidine alkaloids

Heterocycles

Volumn 64, Issue , 2004, Pages 45-50

  Williams, David R ^a   Osterhout, Martin H ^a   Amato, George S ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646869276     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-04-S(P)26     Document Type: Article

References (27)

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23. Less reactive alkenes failed to undergo cyclizations as shown by iodine oxidation of the example below.
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25. B.
26. Carruthers W., Coggins P., and Weston J.B. J. Chem. Soc., Perkin Trans. I (1990) 2323. Carruthers and coworkers prepared bicyclic 12 by 1,3-dipolar cycloaddition en route to alleged andrachamine. However, their claim of a total synthesis was proven to be incorrect following our studies which conclusively demonstrated the misassignment of the natural product. These efforts demonstrated the conversion of 13 (from 8) to the diastereomeric alcohol (14), which was shown to be identical to the product of N-O reduction from 12. See
27. Osterhout M.H. Ph.D. Thesis (1991), Indiana University, Department of Chemistry, Weinheim. Carruthers and coworkers prepared bicyclic 12 by 1,3-dipolar cycloaddition en route to alleged andrachamine. However, their claim of a total synthesis was proven to be incorrect following our studies which conclusively demonstrated the misassignment of the natural product. These efforts demonstrated the conversion of 13 (from 8) to the diastereomeric alcohol (14), which was shown to be identical to the product of N-O reduction from 12. See