A New Route for the Synthesis of 5-Methoxychroman-3-one

Rapid Access to Chroman‐3‐ones through Gold‐Catalyzed Oxidation of Propargyl Aryl Ethers

“…[6] In his 1991 review, [7] Kirkiacharian concluded that there was a lack of efficient synthetic methods for this structure. Since then, little progress [8] has been made. To date, the 20-year old statement still stays largely true.…”

Rapid Access to Chroman‐3‐ones through Gold‐Catalyzed Oxidation of Propargyl Aryl Ethers

“…In their 1991 review,7 Danan and Kirkiacharian concluded that there was a lack of efficient synthetic methods for this structure. Since then, little progress8 has been made. To date, the 20 year old statement still remains largely true.…”

Total Synthesis of Maoecrystal V: Early-Stage C–H Functionalization and Lactone Assembly by Radical Cyclization

“…The preparation of the substrate for the early C–H functionalization reaction began with alkylation of sesamol using 3-(4-methoxybenzyloxy)-2,2-dimethyl-1-propanol ( 6 ) in the presence of diisopropyl azodicarboxylate and triphenylphosphine, 11 which afforded aryl ether 7 in 79% yield (Scheme 2). Its directed ortho -metalation with n -butyllithium in THF, followed by transmetalation to the arylzinc reagent and coupling with methyl chlorooxaloacetate, afforded α-keto ester 8 , 12 which was converted directly to α-diazoester 9 . 13 The essential C–H-insertion was achieved by treatment of 9 with rhodium acetate that provided the benzofuran product 10 in 74% yield and >10:1 diastereoselectivity in favor of the trans -substituted isomer.…”