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

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

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 United States 01.01.2021
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 , and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., ). Simple syntheses of natural products such as ayapin ( ) and scoparone ( ) 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 into the isomeric 2 -chromene precocene I ( ), a naturally occurring inhibitor of juvenile hormone biosynthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02011