Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen

Roswitha Stejskal; Ernst Urban; Horst Völlenkle

doi:10.1007/BF00809359

Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen

Translated title of the contribution: Synthesis and determination of configuration of potential antimicrobial 5,6-dihydroxyisobenzofuranones

Roswitha Stejskal
, Ernst Urban
, Horst Völlenkle

Department of Pharmaceutical Sciences

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88%) and 7 a (4%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by¹H-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.

Translated title of the contribution	Synthesis and determination of configuration of potential antimicrobial 5,6-dihydroxyisobenzofuranones
Original language	German
Pages (from-to)	145-156
Number of pages	12
Journal	Monatshefte für Chemie Chemical Monthly
Volume	122
Issue number	3
DOIs	https://doi.org/10.1007/BF00809359
Publication status	Published - Mar 1991

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry

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10.1007/BF00809359

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title = "Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen",

abstract = "Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88\%) and 7 a (4\%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by1H-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.",

keywords = "H-NMR spectroscopy, Determination of configuration, Garlicin, Isobenzofuranone, X-ray analysis",

author = "Roswitha Stejskal and Ernst Urban and Horst V{\"o}llenkle",

year = "1991",

month = mar,

doi = "10.1007/BF00809359",

language = "Deutsch",

volume = "122",

pages = "145--156",

journal = "Monatshefte f{\"u}r Chemie Chemical Monthly",

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T1 - Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen

AU - Stejskal, Roswitha

AU - Urban, Ernst

AU - Völlenkle, Horst

PY - 1991/3

Y1 - 1991/3

N2 - Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88%) and 7 a (4%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by1H-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.

AB - Oxidation of isobenzofuranone 1 yielded in a diastereoselective reaction epoxide 2. Acidolysis of 2 resulted in a mixture of trans-glycols 6 a (88%) and 7 a (4%), which were separated by crystallization. The relative configuration of 6 a and 7 a at the chiral centers 3 a, 5, 6, and 7 a was determined by1H-NMR-spectroscopy and X-ray analysis of O-acetylated and 7 a-methylated derivatives.

KW - H-NMR spectroscopy

KW - Determination of configuration

KW - Garlicin

KW - Isobenzofuranone

KW - X-ray analysis

UR - https://www.scopus.com/pages/publications/34249916415

U2 - 10.1007/BF00809359

DO - 10.1007/BF00809359

M3 - Artikel

AN - SCOPUS:34249916415

SN - 0026-9247

VL - 122

SP - 145

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JO - Monatshefte für Chemie Chemical Monthly

JF - Monatshefte für Chemie Chemical Monthly

IS - 3

ER -

Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-Dihydroxyisobenzofuranonen

Abstract

Austrian Fields of Science 2012

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