Higher carbon sugars containing more than 10 carbon atoms in the chain, although occuring very rarley in nature , are important components of some antibiotics. Methodology developed in our laboratory allows to obtain rather easily precursors of type 3, higher sugar enones substituted at both terminal positions with monosaccharide sub-units [1].

Enone 3 was obtained in the reaction of phosphonate 1 with aldehyde 2. Reduction of the carbonyl function provided two stereoisomeric allylic alcohols with the R-isomer predominating. Attempts to invert the configuration at the carbinol center failed and the rearranged compound 6 was obtained as the sole product in this process.

[1] S. Jarosz, J. Carbohydr. Chem., 2001, 20, 93: S. Jarosz, Curr. Org. Chem., 2008, w druku

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/13863 must be provided.

1. Stereoselective synthesis of highly oxygenated derivatives decalins and cyclohexanes from monosaccharides
2. Polyhydroxylated decalin derivatives – stereoselective approach from simple sugars via allyltin compounds