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 language | English |
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Pages (from-to) | 6736-6738 |
Number of pages | 3 |
Journal | Tetrahedron Letters |
Volume | 52 |
Issue number | 50 |
DOIs | |
Publication status | Published - 14 Dec 2011 |
MoE publication type | A1 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