Enantioselective synthesis of Boc-protected norfuranomycins

Mikko Passiniemi; Ari M. P. Koskinen

doi:10.1016/j.tetlet.2011.10.007

Enantioselective synthesis of Boc-protected norfuranomycins

Mikko Passiniemi, Ari M. P. Koskinen^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-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 language	English
Pages (from-to)	6736-6738
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2011.10.007
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

Access to Document

10.1016/j.tetlet.2011.10.007

Cite this

@article{3d14a3c570424870b4a798a985273374,

title = "Enantioselective synthesis of Boc-protected norfuranomycins",

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.",

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

author = "Mikko Passiniemi and Koskinen, {Ari M. P.}",

year = "2011",

month = dec,

day = "14",

doi = "10.1016/j.tetlet.2011.10.007",

language = "English",

volume = "52",

pages = "6736--6738",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "50",

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TY - JOUR

T1 - Enantioselective synthesis of Boc-protected norfuranomycins

AU - Passiniemi, Mikko

AU - Koskinen, Ari M. P.

PY - 2011/12/14

Y1 - 2011/12/14

N2 - 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.

AB - 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.

KW - Amino acids

KW - Enantioselective synthesis

KW - Asymmetric synthesis

KW - Natural product

KW - DIMETHYL-SULFOXIDE

KW - SECONDARY ALCOHOLS

KW - OXALYL CHLORIDE

KW - OXIDATION

KW - FURANOMYCIN

KW - (+)-FURANOMYCIN

KW - STEREOISOMERS

KW - DERIVATIVES

KW - ANALOGS

KW - ACID

U2 - 10.1016/j.tetlet.2011.10.007

DO - 10.1016/j.tetlet.2011.10.007

M3 - Article

VL - 52

SP - 6736

EP - 6738

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 50

ER -