Literature DB >> 15496091

An aza-Achmatowicz approach toward the hydroxylated piperidine alkaloids (+/-)-azimic acid and (+/-)-deoxocassine.

Michael P Cassidy1, Albert Padwa.   

Abstract

[reaction: see text] The synthesis of several cis-2,3,6-trisubstituted piperidines has been developed employing the aza-Achmatowicz oxidation as the key reaction step. Its usage is illustrated by the facile synthesis of the piperidin-3-ol alkaloids (+/-)-deoxocassine and (+/-)-azimic acid.

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Year:  2004        PMID： 15496091     DOI： 10.1021/ol048326q

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

2.  Directed aromatic functionalization in natural-product synthesis: Fredericamycin A, nothapodytine B, and topopyrones B and D.

Authors:  Charles Dylan Turner; Marco A Ciufolini
Journal:  Beilstein J Org Chem       Date:  2011-10-28       Impact factor: 2.883

3.  Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives.

Authors:  Andrew Kennedy; Adam Nelson; Alexis Perry
Journal:  Beilstein J Org Chem       Date:  2005-08-26       Impact factor: 2.883
  3 in total

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