Bioinspired Synthesis of Juglorubin from Juglomycin C

In this paper, the synthesis of juglorubin, a natural red dye, from juglomycin C, a plausible biogenetic precursor, is reported. Sequential intermolecular and intramolecular Michael additions of juglomycin C, oxidation, and skeletal transformation proceeded in phosphate buffer to afford an undehydra...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 20; no. 4; pp. 1082 - 1085
Main Authors Kamo, Shogo, Kuramochi, Kouji, Tsubaki, Kazunori
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.02.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Molecular Structure
Naphthoquinones - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
HYDROGEN-PEROXIDE
JUGLORESCEIN
BIOSYNTHESIS
JUGLOCOMBINS
Online AccessGet full text

Cover

More Information
Summary:In this paper, the synthesis of juglorubin, a natural red dye, from juglomycin C, a plausible biogenetic precursor, is reported. Sequential intermolecular and intramolecular Michael additions of juglomycin C, oxidation, and skeletal transformation proceeded in phosphate buffer to afford an undehydrated derivative of juglorubin. Subsequent dehydration of the secondary alcohol afforded juglorubin. The one-pot synthesis of juglorubin from juglomycin C was also achieved. The photophysical properties of synthetic juglorubin and its derivatives were evaluated.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b04051