Synthesis of Coumestrol and Aureol

A total synthesis of coumestrol (1) and aureol (2) is described. The Perkin condensation of 2-bromo-4-hydroxylphenylacetic acid (6) and o-hydroxybenzaldehydes (7) gave the corresponding 2′-bromo-3-arylcoumarins (9). A copper-catalyzed consecutive hydroxylation and aerobic oxidative coupling of 9 und...

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Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 79; no. 10; pp. 2749 - 2753
Main Authors Sheng, Jianfei, Xu, Tianlong, Zhang, Ensheng, Zhang, Xuejing, Wei, Wentao, Zou, Yong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 28.10.2016
Amer Chemical Soc
Subjects
Catalysis
Chemistry, Medicinal
Copper - chemistry
Coumarins - chemistry
Coumestrol - chemical synthesis
Coumestrol - chemistry
Life Sciences & Biomedicine
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
ONE-POT CONSTRUCTION
MICROWAVE CONDITIONS
INHIBITION
ACIDS SYNTHESIS
EFFICIENT SYNTHESIS
ISOFLAVONOIDS
PSORALIDIN
DERIVATIVES
ESTROGEN-RECEPTOR
BENZOFURAN
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Summary:A total synthesis of coumestrol (1) and aureol (2) is described. The Perkin condensation of 2-bromo-4-hydroxylphenylacetic acid (6) and o-hydroxybenzaldehydes (7) gave the corresponding 2′-bromo-3-arylcoumarins (9). A copper-catalyzed consecutive hydroxylation and aerobic oxidative coupling of 9 under microwave conditions facilitated the total synthesis of 1 and 2, respectively, with spectroscopic data highly similar to those of natural products.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00510