Phenazines and natural products; novel synthesis of saphenic acid

Lars Petersen; Knud J. Jensen; John Nielsen

Phenazines and natural products; novel synthesis of saphenic acid

Lars Petersen, Knud J. Jensen, John Nielsen^*

^*Corresponding author for this work

Department of Chemistry

10 Citations (Scopus)

Abstract

The natural product saphenic acid (6-(1-hydroxyethyl)1- phenazinecarboxylic acid) was synthesized from readily accessible starting materials. The desired product was obtained in an overall yield of 22% for four steps with the key steps being formation of a diphenylamine, followed by cyclization under alkaline and reducing conditions. Assignments of ¹H NMR spectra were achieved by homo- and heteronuclear 1D and 2D correlations. Double pulsed field gradient spin-echo one-dimensional NOESY proved especially valuable for assignment of aromatic protons.

Original language	English
Journal	Synthesis
Issue number	10
Pages (from-to)	1763-1766
Number of pages	4
ISSN	0039-7881
Publication status	Published - 1 Jan 1999

Keywords

Antibiotics
DPFGSE-NOE
Heterocycles
Natural products
Phenazine

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title = "Phenazines and natural products; novel synthesis of saphenic acid",

abstract = "The natural product saphenic acid (6-(1-hydroxyethyl)1- phenazinecarboxylic acid) was synthesized from readily accessible starting materials. The desired product was obtained in an overall yield of 22% for four steps with the key steps being formation of a diphenylamine, followed by cyclization under alkaline and reducing conditions. Assignments of 1H NMR spectra were achieved by homo- and heteronuclear 1D and 2D correlations. Double pulsed field gradient spin-echo one-dimensional NOESY proved especially valuable for assignment of aromatic protons.",

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author = "Lars Petersen and Jensen, {Knud J.} and John Nielsen",

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TY - JOUR

T1 - Phenazines and natural products; novel synthesis of saphenic acid

AU - Petersen, Lars

AU - Jensen, Knud J.

AU - Nielsen, John

PY - 1999/1/1

Y1 - 1999/1/1

N2 - The natural product saphenic acid (6-(1-hydroxyethyl)1- phenazinecarboxylic acid) was synthesized from readily accessible starting materials. The desired product was obtained in an overall yield of 22% for four steps with the key steps being formation of a diphenylamine, followed by cyclization under alkaline and reducing conditions. Assignments of 1H NMR spectra were achieved by homo- and heteronuclear 1D and 2D correlations. Double pulsed field gradient spin-echo one-dimensional NOESY proved especially valuable for assignment of aromatic protons.

AB - The natural product saphenic acid (6-(1-hydroxyethyl)1- phenazinecarboxylic acid) was synthesized from readily accessible starting materials. The desired product was obtained in an overall yield of 22% for four steps with the key steps being formation of a diphenylamine, followed by cyclization under alkaline and reducing conditions. Assignments of 1H NMR spectra were achieved by homo- and heteronuclear 1D and 2D correlations. Double pulsed field gradient spin-echo one-dimensional NOESY proved especially valuable for assignment of aromatic protons.

KW - Antibiotics

KW - DPFGSE-NOE

KW - Heterocycles

KW - Natural products

KW - Phenazine

M3 - Journal article

AN - SCOPUS:0032877132

SN - 0039-7881

SP - 1763

EP - 1766

JO - Synthesis

JF - Synthesis

IS - 10

ER -

Phenazines and natural products; novel synthesis of saphenic acid

Abstract

Keywords

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