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 af dette arbejde

Kemisk Institut

10 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Synthesis
Udgave nummer	10
Sider (fra-til)	1763-1766
Antal sider	4
ISSN	0039-7881
Status	Udgivet - 1 jan. 1999

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Citationsformater

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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.",

keywords = "Antibiotics, DPFGSE-NOE, Heterocycles, Natural products, Phenazine",

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

year = "1999",

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language = "English",

pages = "1763--1766",

journal = "Synthesis (Germany)",

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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 (Germany)

JF - Synthesis (Germany)

IS - 10

ER -

Phenazines and natural products; novel synthesis of saphenic acid

Abstract

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