Enantioselective synthesis of Boc-protected norfuranomycins

Mikko Passiniemi, Ari M. P. Koskinen*

*Corresponding author for this work

    Research output: Contribution to journalArticleScientificpeer-review

    4 Citations (Scopus)

    Abstract

    Garner's aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for a-amino alcohols avoiding epimerization of the labile a-proton of the product aldehyde. (C) 2011 Elsevier Ltd. All rights reserved.

    Original languageEnglish
    Pages (from-to)6736-6738
    Number of pages3
    JournalTetrahedron Letters
    Volume52
    Issue number50
    DOIs
    Publication statusPublished - 14 Dec 2011
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Amino acids
    • Enantioselective synthesis
    • Asymmetric synthesis
    • Natural product
    • DIMETHYL-SULFOXIDE
    • SECONDARY ALCOHOLS
    • OXALYL CHLORIDE
    • OXIDATION
    • FURANOMYCIN
    • (+)-FURANOMYCIN
    • STEREOISOMERS
    • DERIVATIVES
    • ANALOGS
    • ACID

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