Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

Anna Edelsbacher; Ernst Urban; Waltraud Weidenauer

doi:10.1007/BF00812323

Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

Anna Edelsbacher
, Ernst Urban
, Waltraud Weidenauer

Department of Pharmaceutical Sciences

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO₄ and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optic ally puredihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

Original language	English
Pages (from-to)	741-747
Number of pages	7
Journal	Monatshefte für Chemie Chemical Monthly
Volume	123
Issue number	8-9
DOIs	https://doi.org/10.1007/BF00812323
Publication status	Published - Aug 1992

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry

Keywords

Diastereoselective synthesis
Garlicin
Isobenzofuranone
Lactones

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10.1007/BF00812323

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title = "Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones",

abstract = "Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO4 and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optic ally puredihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.",

keywords = "Diastereoselective synthesis, Garlicin, Isobenzofuranone, Lactones",

author = "Anna Edelsbacher and Ernst Urban and Waltraud Weidenauer",

year = "1992",

month = aug,

doi = "10.1007/BF00812323",

language = "English",

volume = "123",

pages = "741--747",

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

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T1 - Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

AU - Edelsbacher, Anna

AU - Urban, Ernst

AU - Weidenauer, Waltraud

PY - 1992/8

Y1 - 1992/8

N2 - Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO4 and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optic ally puredihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

AB - Optically pure available lactones 1 and 5 were diastereoselectively oxidised to cis-diols 2 and 6 by KMnO4 and to epoxides 3 and 7 by 3-chloroperoxybenzoic acid. Epoxide 3 was cleaved to trans-diol 4, whereas hydrolysis of 7 afforded tricyclic carboxylic acid 8. Optic ally puredihydroxylactones 2, 4, and 6 are valuable models for structure determination of the antimicrobial garlic component garlicin.

KW - Diastereoselective synthesis

KW - Garlicin

KW - Isobenzofuranone

KW - Lactones

UR - https://www.scopus.com/pages/publications/0041073053

U2 - 10.1007/BF00812323

DO - 10.1007/BF00812323

M3 - Article

AN - SCOPUS:0041073053

SN - 0026-9247

VL - 123

SP - 741

EP - 747

JO - Monatshefte für Chemie Chemical Monthly

JF - Monatshefte für Chemie Chemical Monthly

IS - 8-9

ER -

Preparation of enantiomerically pure 5,6-dihydroxy-isobenzofuranones and 5,6-dihydroxy-4,7-methano-isobenzofuranones

Abstract

Austrian Fields of Science 2012

Keywords

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