The Journal of organic chemistry

Synthesis of 2, 3-dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from epoxy aldehydes. One-step syntheses of brosimacutin G, vaginidiol, vaginol, smyrindiol, …

Y Zou, M Lobera, BB Snider

Index: Zou, Yefen; Lobera, Mercedes; Snider, Barry B. Journal of Organic Chemistry, 2005 , vol. 70, # 5 p. 1761 - 1770

Full Text: HTML

Citation Number: 33

Abstract

We have developed two practical one-step syntheses of 2, 3-dihydro-3-hydroxy-2- hydroxyalkylbenzofurans from readily available optically pure α, β-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy ...