The new phenols 6-oxo-tingenol, 3-O-methyl-6-oxo-tingenol and 6-oxo-iguesterol were isolated from the root bark of Maytenus canariensis. Their structures were determined by 1H and 13C NMR spectroscopic studies, including HMQC, HMBC, DEPT and ROESY and chemical transformations. The synthesis of 6-oxo-tingenol was achieved from tingenone. These compounds exhibit antibiotic activity against Gram-positive bacteria.