Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2H‑Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au­(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) a...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 1; pp. 178 - 198
Main Authors Cervi, Aymeric, Vo, Yen, Chai, Christina L. L, Banwell, Martin G, Lan, Ping, Willis, Anthony C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
MILD
ACID
SOLID-PHASE SYNTHESIS
ANALOGS
CATALYZED HYDROARYLATION
EFFICIENT
RING-CLOSURE
CYCLIZATION
ALKENYLATION
Online AccessGet full text

Cover

More Information
Summary:Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au­(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02011