Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives 尾-(hydroxymethylaryl/alkyl)-伪-methylene-纬-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (卤)-hydroxymatairesinol (8) and (卤)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization, respectively.