A concise synthetic route to the conduritols from pentoses.
A short synthetic strategy for preparation of the conduritols is described. The key step employs a zinc-mediated fragmentation of protected methyl 5-deoxy-5-iodo-d-pentofuranosides followed by an allylation of the intermediate aldehyde in the same pot. The allylation is performed with 3-bromopropenyl benzoate and occurs with good diastereoselectivity. An amino group can be introduced in the product by trapping the intermediate aldehyde as the imine prior to the allylation. The functionalised 1,7-octadienes, thus obtained, are converted into protected conduritols by ring-closing olefin metathesis.
Keinicke
Lise
L
Center for Sustainable and Green Chemistry, Department of Chemistry, Building 201, Technical University of Denmark, DK-2800, Lyngby, Denmark.
Madsen
Robert
R
D003500:Cyclization; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010429:Pentoses / Q000737:chemistry*
D003511:Cyclohexanols; D010429:Pentoses