An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization.
[reaction: see text] The iodocyclization of acetoxy-containing 2-(1-alkynyl)anisoles and subsequent direct palladium-catalyzed carbonylation/lactonization provide an efficient route to naturally occurring coumestan and coumestrol, and their related analogues.
Yao
Tuanli
T
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Yue
Dawei
D
Larock
Richard C
RC
D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003375:Coumestrol / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D003374:Coumarins; D010165:Palladium; D007455:Iodine; C505898:coumestan; D003375:Coumestrol