A concise synthetic route to the conduritols from pentoses

Lise Edelmann Keinicke, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume3
Issue number22
Pages (from-to)4124-4128
ISSN1477-0520
DOIs
Publication statusPublished - 2005

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