TY - JOUR
T1 - Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes
AU - Cervi, Aymeric
AU - Vo, Yen
AU - Chai, Christina L.L.
AU - Banwell, Martin G.
AU - Lan, Ping
AU - Willis, Anthony C.
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2021/1/1
Y1 - 2021/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85097823726&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c02011
DO - 10.1021/acs.joc.0c02011
M3 - Article
SN - 0022-3263
VL - 86
SP - 178
EP - 198
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -